@Ross Bowman Thanks man! No worries glad you commented!
So far it has gone extremely well, beating my expectations in the first 4 month even as we are in the Fall, not the peak of summer. The cabin I truly believe is able to appeal to travelers in any season though, given the location.
I currently am continuing that, have some new roommates moving in this Friday to househack with me, so they will be paying my entire mortgage (minus 50 bucks) to live here with me in my primary, and I too am under contract with a partner for another STR in PCB,FL ! We close a week from today!
I would say it's not as scary as it seems, it's not as hard as it seems, just have an exit strategy for worst case scenario, but man I love STRs. I'm not sure how you are managing, be it self managing or hiring out, but I would suggest to self manage. I plan to do that to my cabin property in the near future, to save that 10% that I'm paying to Evolve to manage. Evolve is cool and was a great starter management company to use, but what I found to be true is while yes, they created the listings, hired the photographer for the first time, and used their automated systems to send guests check in information, request reviews, etc. That isn't THAT much work. Additionally, I still find myself talking to almost every, if not every guest. I am the problem solver, I also look to build relationships with every guest. I think that truly makes a difference. Don't overdo it, but be a human, imagine what you have liked from hosts in past places that you've stayed.
Additionally, one of the MOST important things is your cleaning partner. Maintenance partner is also important, especially for my cabin as it's on 24 acres and he has maintained all of that for me. The cleaning WILL make or break you. Reviews and reputation are everything, and again, just imagine what you would do if you went to vacation and popped up in a nasty place. No one wants that!
I owe so much of my small bit of success so far to my cleaning and maintenance partners. I call them partners, as that's how I view it. Without them I would not be doing nearly as well. My last piece of advice, take care of them, they'll take care of you.
I often throw in little bonuses to them, got them a customized cutting board with their names for their home, etc etc. That kind of stuff matters, be authentic, be genuine.
Hope this helps brother.
-Alec