Hi @Brian Davis,
Howdy, neighbor! We live in RI and are doing a bit of what you describe. We have long term rentals here in RI/MA and short term rentals in Myrtle Beach and Gatlinburg.
It's awesome to have a place you can use whenever you want, but think about how you will get there. A short drive to the Cape, New Hampshire, lakes region of NY, etc is easy. Think about how far you are realistically willing to drive, flight availability out of your regional airport, etc. We love our MB condo and don't regret anything about it, but flying down there a few times a year (with connecting flights and the unpredictability of air travel) isn't enjoyable.
As far as the Cape goes, they aren't building any more beaches last I checked, so I think those price points are here to stay and will only go up over time.
Being a property owner anywhere is work (but this is a giant forum of people who love doing it, including myself), so you're on the right track in educating yourself and learning. Good luck on your journey!