A friend of mine in Austin once negotiated a partial buy back option when the seller realized they might want back in if the market soared.. from what I read in Bloomberg, that approach can work well if both sides trust each other.If the tenants’ rent covers your carrying costs, that’s a nice cushion, but you still need to clarify that buy back clause.

To list a few...Anyone who wants to increase their property’s income potential (and equity) and build new housing in a market that struggles with high prices, low supply, and few new construction.House hackers who live in their primary and want to airbnb an ADU love this strategy or vice versaInvestors who want to do both long term and short term benefit from having two separate units.Rental Restrictions on ADUs.Thankfully, Raleigh is very STR friendly and ADU friendly right now.

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.

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

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.

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

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 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.

Instead of having to enter personal info and upload an image of your driver's license for each Reporting Company, the Individual FinCEN ID allows you to input your personal data once and then link the Individual ID to your various Reporting Companies. 

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.