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As with many areas of financial planning, there is not a blanket statement I can use to tell you where to retire. What I can do is provide you with the resources, tools, and considerations to make the best decision for your situation.
Choosing a place to retire is a big decision and can be a daunting process to begin. To help start this process, I can recommend creating a list of what is important to you in retirement. If you are married, this starting point might have two lists. From your one or two lists you can then compare, contrast, and compromise to establish the main characteristics you are looking for in your retirement destination.
There are two categories of factors that may appear on your list mentioned above. These two categories are the quantitative characteristics and the qualitative characteristics you are looking for in retirement. The quantitative characteristics include items such as house prices, cost of living, and taxes. The qualitative characteristics include proximity to family, proximity to a hospital, the weather/climate, population density, and culture or vibe. It is your job to choose the qualitative aspects that appeal to you (and your spouse) to see if they match up with your quantitative preferences. If they do not align perfectly, it is time to accept a tradeoff to accomplish your main goals.
When starting to brainstorm specific regions or cities to live in, many people gravitate towards a favorable vacation destination. Although this may work for some people, these spots are generally not ideal for long-term living needs. Why is this? These vacation spots generally are set up in a way that caters towards tourist and one-week stays. It may be less enjoyable than you may imagine retiring in a place in which you have fun on vacation.
When you have narrowed your list down to a few areas, consider taking them for a test drive. How better to learn an area than to spend a few weeks in these targeted towns? I would recommend multiple trips, if possible, in order to experience the area during different seasons and times of year. There could be busy summers and empty winters or vice versa. Certain factors to keep an eye on while you are there include the weather, traffic, and how crowded grocery stores, gas stations, and other public locations are on a daily basis.
After you have completed a few of these test drives, go back to your list. Then, start to compare how the reality of the visits compared to expectations. You may eliminate a few options at this point based on your experiences and figure out which aspects of your potential retirement destination are most important. Does the town being extremely tax favorable outweigh the several-hour plane ride you would be from family? Is it worth it to live in a place that is seemly ideal in every way except for the crowded stores and heavy traffic when you leave the house?
It is my hope that through utilizing the thought process outlined above, along with resources linked below, you are able to better approach and evaluate the question of “where should I retire?”