Hi Kayla,
Is this a property you would buy yourself as a vacation home if it wasn't a STR?If the HOA chooses to amend their HOA policy allowing STR, will you be able to cover the mortgage as a LTR with a leased tenant?
We have a ski cabin in Skykomish, WA about 1 hour away from our home. My wife and I spruced it up and listed it on AirBnb and the experience with guests has been very positive. Our cabin is super small and we only allow 2 guests at a time so it doesn't become a party house. Our strategy has worked and it does well to fairly well covering the mortgage each month.
I service the unit and collect the mileage deduction for taxes. I'm a control freak and want the place spotless for guests. I will say the experience is very positive when guests are neat and clean. It gets frustrating when guests are sloppy, messy, spill wine, leave excess trash or put grease down the drain... We've learned a lot and now have the right fixtures and furniture to weather STR impacts.
During the pandemic the ski cabin was rented almost 95% of the time. It printed money for us and we were able to slam the mortgage down and felt like geniuses. Now that the area is super saturated with STR options, it performs well but not stellar. Our goal has always been to cover the mortgage so we'd have a "free cabin."
We've chosen to keep the cabin off AirBnb this winter so we can ski every weekend with the kids. We're giving up some rental revenue, but we're actually busier as a STR in the summer so it should work out.
Having laundry in the unit is a huge help when getting it ready for the next guests. Things like power outages during winter storms, septic clogs due to misplaced products into the toilet have been the biggest issue. It sounds like your passion and vision for the property are indelible so I would encourage you to go for it!
One tip: Don't tell anyone you have a STR! That way friends, family, local non profits and charities won't hit you up to "donate" a week, weekend or getaway. I learned that lesson the hard way!