@Courtney Barnes welcome and congrats on getting started. I have helped dozens of other members purchase STR here. However, most of them are looking for cash flow exclusivley and in turn, I show them home in the resort communities to maximize returns.
Since you mentioned that you may want to retire to the home, a resort community would not be a good fit for you as they are specifically built for STR and every home is used that way. There are plenty of other 'regular' neighborhoods that can still perform to your expectations and needs. I'd be happy to have a call to discuss some options with you.
On the loan side, you mentioned 15-20% down. If this is an investment home, you will be required to put 20% down. If you do it as a second home, you could do less, but then have to carry PMI. That is a conversation to have with a lender and your CPA.
Reach out if I can be of any further help. Where at in Michigan are you in, I'm from Toledo and spent a lot of time there.
Best of luck!