Vacation/Retirement/Investment home--Does anyone here have one?

<p>H and I have one child, a current college sophomore. We have a house that is too big for us. Both of us would like to down-size to a smaller place. BUT we have no plans to retire anytime in the foreseeable future; we both have jobs here that we love. For some reason, though, H has become enamored with the idea of buying a small house or perhaps a condo that would be an investment property that we would rent out, a vacation home for us, and eventually a house we could live in if we ever retire.</p>

<p>Although it sounds like a good idea in theory, does this actually ever work? It seems like with having to pay a management company to be in charge of renting the house out, and the risk of damage from all of those short-term renters, the likelihood that this would be a good investment is uncertain at best . . .</p>

<p><a href=“http://talk.collegeconfidential.com/parent-cafe/1362545-second-home-experience.html[/url]”>http://talk.collegeconfidential.com/parent-cafe/1362545-second-home-experience.html&lt;/a&gt;&lt;/p&gt;

<p>This is exactly what we’ve done. However now we realize that there are too many stairs for us when we get a lot older and probably need to sell it at some point in the future. I rent it out myself and usually don’t have a problem as its near a large university. It still is a hassle from the standpoint of taking care of etc. The past few summers we haven’t used it as we’ve taken extended vacations so I rent it out during the summer also.</p>

<p>We have some friends who sold the large fully paid for family home. They took the proceeds and bought a condo in Florida and a small vacation home in coastal Maine. They, like the OP, we’re not ready to retire or move so they actually rented an apartment in their old town where they live a good chunk of the time. Eventually they will stop working and will spend time between Florida and Maine.</p>

<p>Two years ago we built a second home that we plan to be our full time residence in a couple of years. We don’t rent it out. We use it for weekends/holidays. It’s on the water so we spend a lot of time there in the summers. </p>

<p>In preparation for the eventual move, we sold our paid for home of 23 years in April. We are now living in a rental house just a couple of miles away from our old home.
We used the proceeds from home sale to pay off the mortgage on the second home.<br>
Now when the time is right for us to make a move, we’ll be ready.</p>