Showcase Listing

Cresswind Charleston is Charleston-area's BEST active adult lifestyle community. Cresswind inspires active adults to live life to the ful...

Showcase Listing

Nestled in the foothills of the Great Smoky Mountains, Tellico Village comprises over 5,000 acres along Tellico Lake. Established in 1986...

Showcase Listing

The Grove is an upscale, manufactured home community for active adults 55+, located in sunny Bradenton, Florida, on 40 lush acres of form...

Showcase Listing

Bon Ayre is a 55+ active adult, manufactured home land lease community located in Smyrna, Delaware, a town which was recently ranked 31st...

Showcase Listing

Cresswind Georgia at Twin Lakes is a new, gated 55+ community in the metro Atlanta, Georgia area. With a focus on fitness, relationships,...

Showcase Listing

Fairfield Glade, a stunning master-planned community, is perched high atop the Cumberland Plateau, and offers serene mountain beauty as i...


7 Questions to Ask – Before You Pick a Place to Retire

Category: Retirement Planning

November 12, 2013. — Let’s assume you have been doing all the things the experts suggest as you go through the process of finding your best place to retire. You have listed your priorities, discussed them with spouse and/or family, and paid visits to the more likely suspects. But before you make that down payment on your retirement home, here are 7 more questions we think you would be well advised to answer. Hopefully this list will make you think of a few more, all the better to help you realize the wonderful retirement you have worked so hard to get.

7 Questions to Ask
These questions are meant more as a stimulus for conversation than a yes or no. By discussing them with someone else, you might gain more insight into the kind of retirement it is that you are looking for.

1. Would you rather read a book or play a round of golf?
This pretty easy question shouldn’t just be confined to these 2 choices. What you would like to do with your newly acquire freedom has implications for climate, the available facilities in the area to do them, and what type of community you want to live in. Obviously, pick a place where it’s easy to do what you want. What can be tricky is when a couple has widely different interests – a compromise might be needed.

2. Do you like to be surrounded by other people, or off by yourself?
Obviously, don’t decide to live in the country or mountains if you thrive with many daily social interactions. If you love being around other people, consider a condo or townhome, a small town or city, or an active adult community. If rules aren’t your thing and you think having any neighbor within 2 miles is way too close, you know what to stay away from.
3. Would you like your neighbors to have similar interests to yours?
We see enough comments in the Topretirements Blog to realize that many people are happiest when they are surrounded by like-minded people. Similarly, folks who love golf, tennis, or socializing really prefer being in a community where many people enjoy those same activities. Yet on the other side of the coin are the people who thrive on the stimulation that differences provide. They want to get into a political discussion and debate various sides of the issues. Or they want to be around children and teens, or folks of other ethnicities.

4. Will your children and grandchildren want to visit?
A not unimportant question, assuming that most people want to spend time near their offspring. If you decide to live in a town that is near a family vacation entertainment center (think Central Florida near Disney World) or a popular tourist city, you can probably bank on your family’s regular visits. If on the other hand you choose a 55+ community with limited recreation facilities, you probably won’t have to clean the guest bedroom very often. Which means you will be the one doing the traveling. Or, better yet, perhaps you might be better off finding a place to retire that is close to where your family has settled.

5. What will do if you need a medical specialist with operating privileges in a major league hospital?
As Jan Cullinane astutely observed in the comments to last week’s “Best Small Town for Retirement” article, the quality and proximity of healthcare is an important concern. You might not have any medical conditions now, but if you live long enough you probably will. Driving 3 or 4 hours to visit a specialist can get old, or even be out of the question as you age. Worse yet is having to rely on a medical professional who is out of his or her depth, or not having a choice among top tier providers.

6. How hot and humid can you stand the summer, and how cold the winter?
Many of our visitors and members seem very concerned about humidity (also bugs). Quite a few, including your editor, aren’t that crazy about cold weather. It’s your retirement, so why not choose the kind of climate that makes you happy. But one caution here – please don’t rely on what you might have heard from someone else about how bad the weather is in a place you might otherwise be attracted to. If you really like the area for other reasons, go spend some time there and judge for yourself. You might just be surprised. Again, this can be a troublesome for couples with very different opinions on climate.

7. What’s your plan for the day you can’t drive anymore?
The smartest retirement planning includes the long term view. The typical retiree is active and mobile in their mid-60’s. Twenty to thirty years later, the probability is that many of us will still be kicking. But we might not be able to drive anymore, and many of us will have mobility issues. Planning for a graceful transition to old age, one that doesn’t require a big move down the road, is an important consideration. One solution is to pick a community that has assisted living or a CCRC nearby, so the inevitable move is not too traumatic. Or to pick somewhere where the universal design features, or set up of the community, encourage people to stay in their homes safely and comfortably.

Comments anyone? Are there other questions you can think of? Which one of these presents the greatest difficulty for you or your spouse or friend? Please share your thoughts about the right questions to ask – before you place to retire – in the Comments section below.

For further reading:
How Ready Are You for Retirement Quiz
Is This the Right Time for You to Retire Quiz
Successful Retirement Countdown: 8 Steps to Success

Posted by Admin on November 12th, 2013


  1. What is the status and future plan for the municipality you will be part of? What is the plan for the future? What is the projected growth over the next 20 years? Are the services available that you need? As we age we may need mre medical and health related services. Are those services close by? If you are 60 now, recognize that your needs and desires will change as you age. If you are a couple and something happens to one of you, is this a place the other would want or could handle easily?

    by David Lane — November 13, 2013

  2. I think David Lane has a valid add-on consideration to consider. Two things we already know: our children, grandchildren, great-grandchildren are scattered all over the US so that’s one point we don’t have to ‘discuss’; the 2nd being having to drive 4 hours ( or even 2 hours)- been there, done that – wouldn’t wish it on anyone. The first couple of times included new scenery, a new town to investigate and then …. well, let’s just say our car knew the way. If you should get cancer, this will be your lifestyle for awhile if you don’t live near good medical facilities. If you’re fortunate to live as we both have. I think living in a college town that has a medical school w/a good reputation would be a good idea. I would think the town/city’s future would be fairly steady & should have all the latest & greatest amenities, including decent hotels for visiting relatives should you need that.

    by Jeanne C — November 13, 2013

  3. Do you have a prioritized questionnaire that results in a list of sorted locations?

    by Don Vail — November 13, 2013

  4. In line with assisted living availability a good home healthcare organization would also be helpful in a transition period to help extend the time one can safely remain in their own home. I was the chairman of the board for a home healthcare organization in New England for several years and saw that the move to any facility out of the home was, most of the time, a traumatic experience. Actually being in an area that has both good home healthcare and assisted living facilities is an important factor for a couple because the trauma is high for both even if one remains in the home. If the visit is close and easy for the partner still at home many times the stay in the assisted living facility may not be permanent. The availability of both services makes it easier for the health and wellbeing of both partners.

    by Dan — November 13, 2013

  5. As I’m sure is the case with many retirees, my wife and I have some differences between us and some subsequent compromises to make. With that said, I still have not found the definitive guide to choosing the right place or a mostly pertinent list of questions to use. One geographic location will not necessarily be ideal, since our kids are already in widely dispersed locations. My wife and I are 7 years apart in age, and therefore our perceived needs for retirement (I’m in the zone while she’s still working full time). She’s a home-body and I’m in need of a change. Compounding that, our retirement finances will not allow us to live out our remaining years here in NJ.

    I don’t expect anyone to solve these issues for us but ideas on how to tackle the various obstacles would be really helpful.

    by DanD — November 13, 2013

  6. My top concerns are the level of medical services available to me. Is the hospital where I might move at the same level as my current hospital? How about heart specialists, respiratory specialists, surgeons , primary care, counseling, Rehab centers, etc. Those considerations trump school and real estate taxes. Ed T.

    by Ed Tootill — November 13, 2013

  7. Cost of living is tops with me. If the cost of living is low, I can make a lot of things better — live in a better neighborhood, etc.

    by Mark Terry — November 13, 2013

  8. Dan D and I have very similar issues. My wife is 9 years younger and I am almost 70. We have to get out of our empty 4 bedroom house in expensive and crowded Northern VA. My children are in this area with our first grandchild expected in 3 months. I feel anxious about leaving my Doctors and specialists. I want so much to go to a warmer climate or maybe back to (colder) a central PA college town. My wife says she is willing to go where-ever but I know she really doesn’t want to go as far as Florida. The only 3 things we know for sure is that we want a smaller home with a ground floor Master bedroom, a community with amenities and a place we can develop friends and a social life. I worry about making a wrong move and regretting it later. One issue is that we just don’t have a good feel for how much involvement we will have with our new grandson when he gets here as our daughter stays involved with her younger friends and does not seem to want to spend any real time with us thus far…maybe that will change. How can we ever decide where?

    by Bruce V — November 13, 2013

  9. Air transportation to key relatives;
    Crime statistics;
    Attitude of locals to “Newcomers”;
    recreational activities;
    Ave Cost of living indexed to some benchmark;
    Ave cost of housing (buying & renting)

    by D Ackerman — November 14, 2013

  10. My financial advisor is suggesting buying a house where we are retiring ( in another state) now, while I am still working in order to get a mortgage. This concerns me because I feel I should rent for the 1st year to get a feel for the area, make sure I like it and to know exactly where I want to buy a house, I would love to hear comments, ideas and experiences please.

    by Jim Curren — November 14, 2013

  11. Great questions and very empathetic with all the comments. My husband is 62, 9 years older than I, so wherever we look has to be able to provide me (a nurse) with a good job with benefits. Also, we have to limit our search to low cost of living, so we are concentrating on states with no income tax at this point. Staying in IL is out of the question. Presently we are drawn to the Spokane area of Washington, and are planning a visit soon. Anyone out there with inside info on retiring there?

    by Patty D — November 14, 2013

  12. Excellent article, and great comments. I learn from all of you. I’ve worked in the public safety sector my career, so as we evaluate where to retire, I look at the police, fire, and EMS services. Where we live outside Anchorage, Alaska)the fire & EMS responders are volunteers. Not a good place to need an ambulance, as it may take a while to arrive. Also, I am looking at the costs of medical care. We are both healthy now (thank God) but I know that medical costs in the Anchorage area are at least 30-40% more expensive than in the Lower 48 states. So even with health insurance, can I afford a lengthy illness?

    by Jon O — November 14, 2013

  13. to Patty D: A lot of retirement sites mention the fact that Alaska doesn’t have a state income tax (true); that we receive an annual dividend from the state (true, at least for now). But be wary about considering AK as a retirement state, due to the costs of medical insurance and medical care, and due to the high costs of EVERYTHING else. It’s just not a good financial choice. Washington state doesn’t have an income tax but I understand some other taxes are fairly high. That said, we’re looking at the olymnpic peninsula in WA.

    by Jon O — November 14, 2013

  14. My company has a lot of people in their 60s, and we’re all debating “where to retire.” Some are sure they want to stay in their communities, and others are looking at Florida, South Carolina and North Carolina (apparently top options for many of them, particularly the folk from NY, NJ and Mass. The idea of being within an hour of a beach is attractive. I have been asking for their opinions about staying near family. My kids are still in their 20s, so I’ve been particularly interested in the opinions of people whose kids are more established. I’m hearing almost the same thing that I’ve picked up here, which is either that their kids are so busy they just don’t see them as much as expected or they are becoming babysitters. (Heck, I wouldn’t mind babysitting grandkids but 2 of my kids are still in college and grad school…so no babies yet, I hope.) Everyone is concluding that we should go ahead and pick the place where we want to be, at least for the first 10 years or so of retirement when we’re presumably healthy enough to enjoy being in that location.

    The options are still overwhelming, since I don’t have a particular dream location. I’m trying to figure out net cost of living, which would mean more disposable money to do other things. I’m also looking at cost of housing. Being able to spend something in the range of $200,000-$250,000 will mean more cash in my pocket for lifestyle. I haven’t decided yet on 55 or older housing. On the one hand, I like the idea of activities and like-minded people. On the other hand, I don’t want be in a community where everyone is aging in place. Once the baby-boom is over, I don’t know how much value all of those large 55+ communities are going to hold, which is relevant if my kids inherit my home. I sorta like the idea of Orlando, since I assume my kids will visit at least once a year for the amusement parks or on their way to cruise ports. I also like the idea of being near beaches, since I grew up near Long Island Sound. I’m a new widow, so whatever I do will be a single adventure.

    Anyway, I just wanted to say that I really like this site, and I appreciate everyone who posts. I’m always picking up some new ideas or perspectives. I often go from here to, trulia or particular community websites to research locations that are mentioned. Thank you all.

    by Sharon — November 15, 2013

  15. Jim Curren- friends retired in the past year and received the same advice from their financial advisor. Even though they were financially secure with a seven figure investment portfolio, two pensions and one disability pension, they were told to keep their money earning money, and to take a mortgage for their new home in NC. Mortgage rates were much lower thanntheir investment returns. The hassle began as they met with mortgage lenders – many refused the application as they were retired. A mortgage in retirement does not appeal to me or my husband in any way! Our friends ended up using Quicken Loans after many denials from banks and mortgage companies – hope that helps!

    by SandyZ — November 15, 2013

  16. To Jim Curren, don’t rely on your financial advisor for everything. Look at how he lives and go from there. If he rides a bus to work, I would look again. His advice might just be the stats out of a book, not the real world. You must always check the waters and see how YOU feel about it. Remember he is playing with YOUR money not HIS. It makes a big difference. Renting will only cost you a months rent. I agree, buying is always a better idea while working. But buying and getting stuck is no fun. Takes the enjoyment out of retirement. It’s YOUR money, get the best bang for the buck and spend wisely, once.

    by charlie — November 15, 2013

  17. Jim Curren, your financial adviser is indeed telling you a good approach to max out your money. Mortgages are still pretty cheap right now and you will be easier to approve while working. But choosing where you want to spend your retirement is not based on financials alone, or we would all pick the cheapest arm pit of the world to move to.

    And consider the loss of income on the funds you need to put into the house purchase, which between down payment and escrows can be substantial. Need furniture for that second place? Add that to the dollars you would be spending then figure out what you would lose in income from that dollar amount by calculating what your FP would earn for you. How much rent would the income from those funds pay, year after year? Buying is only one option.

    We are doing something of a combination of strategies, buying a small cabin a few years before our trigger date for retirement where we have vacationed for years. It is however pretty rural and far from just about everything, so will work best as a three season home in the first 10-15 years of retirement. For winter we expect we will spend most of that time traveling and looking for where we want to be when there is a bigger need to settle down closer to facilities. I confess I am looking forward to settling into a different place every year, renting a furnished home via a site like for a few months, and then heading home to our cabin. I don’t want to gyp myself of that adventure.

    by Julie — November 15, 2013

  18. The other thing you can’t get, at least not easily, is new credit cards when you are no longer working. So pick and choose the ones you want while you can!

    by Lulu — December 3, 2013

  19. I haven’t had any problem getting new credit cards and I’ve been retired for over 3 years. All it takes is an excellent credit rating and FICO score.

    by Linda — December 4, 2013

  20. I just signed up. I do my own investing. Made 37% this year and 25% last year. My FP can’t match my returns and says I’m the most aggressive investor she’s ever met. Wife and I are just starting our retirement landing spot in Northern FL. I will not let a FP handle my finances because they don’t look out for me, they look out for them. I can easily do 20% a year. WE are going back down in July to see how hot Northern FL can get. No I won’t invest your $.

    by Joe S. — January 5, 2014

  21. All of the above questions and shared information are interesting and quite helpful. Seems like we can’t get enough information to make this enormous transition and move. I’m a young (thank God) 71 year old single woman living a very physically active life in Southern California. My challenge: finding a place that offers many opportunities for an outdoor life. My problem: a limited budget. My Mom forever and a day emphasized good-to-great medical facilities and doctors as we get older. She was right, so that is on the non-negotiable list.
    What I already know about trying to be near family is that they are still young enough, still subject to a move related to work, and grandchildren grow up and on with their lives. I’m about ready to move (next year or so), but my son’s work keeps him based in Southern Calif. They may or may not relocate eight years from now (place unknown), so trying to be within a reasonable drive of them means a higher cost of living. What will give us the greatest comfort and enjoyment during our remaining healthy, active years……? That, coupled with budget and health-care may be my top consideration.

    by Shelley P — February 27, 2019

RSS feed for comments on this post. TrackBack URL

Leave a comment