@Robert SchwenklerI only operate 1 STR which began Memorial Day weekend.

But there are many communities nearby which will allow you and your boys to make memories, and eventually you can retire here.

A well-crafted listing description highlighting the home’s features and recent upgrades can further entice buyers.

So, many have to be pushed into allowing them and then have "memory problems" or "forget" to tell the other occupants.This is the NUMBER ONE REASON for no showings until accepted offer.

Will they make memories?  

Materially participate in crafting your goal(s), your plan (working backwards from your specified goal(s).  

.$168.88 Simmons Premium Hybrid Memory Foam Mattress 10" - https://www.amazon.com/gp/product/B09PFJNFV4/ref=sw_img_1Could be a good mattress.

I want to give back to the City that gave me so many good memories.

Memorial Day to Labor Day will pretty much take care of itself, but adding in amenities like a hot tub and a sauna will help you draw in more traffic and bookings even when there's a foot of snow on the ground.Just to touch on the LTR option, I don't know if this would get you the kind of returns you'd be looking for to even cover your mortgage, let alone cover any maintenance/capex/management costs the property might require. 

Quote from @Allison Craft: Prosper is very expensive in my opinion, especially when starting out.