I was in a similar position a few years ago, but fortunately got married and our combined incomes helped us qualify for a larger house hack.We're on our second one in NOVA, Alexandria to be exact, and instead of rent by the room, we are renting out our walkout basement on Airbnb to monthly guests.That said, we have a number of friends doing well with rent by the room across NOVA, though they're purchasing homes with 5+ rooms or finding homes that can be renovated to include that setup.I'd recommend attending meetups such as the one I cohost, NOVA REI or Cashflow Breakfast Club or any of the others to meet those who are house hacking.

The owners became friends with the tenants and do not feel comfortable raising rents on their friends. 

All of this said, be sure to do your research on STR regulations first and find a STR friendly location.

I recommend you go visit a few times to network with local investors or find an investor friendly agent so you can gain local market knowledge, find off market deals and for things such as showings, picture taking or getting accurate comps.

My first impression is that your numbers in the current economic climate seem a little rosy.I also have friends that are builders and I try to stay in touch with them on costs as we mostly do "to the studs" renovations when we buy a place. 

I was envious of a friends big gorgeous fixers in Arkansas, and I reacted by over-renovating, holding on too long, getting over-leveraged and then 2008 happened and…well enough said.

Now as I stated I'm not a agent but I do feel confident in this here friend. 

Quote from @Andrew Steffens: Sorry about your frustrating issue - Airbnb is not only guest friendly but most of the time they will be the one paying for damage so they are going to try to minimize you. 

Smart move. documentation is your best friend :)  Stay safe out there.

I know in Virginia my friend had a similar issue (side-by-side duplex, though, not second floor) and he was not proactive, just warning them several times verbally.