You can submit comps to support your asking price but it is not guaranteed.

If they support a rent increase, you could look into raising your rents by that amount to offset the cost.

Personally, if your market tends toward the former condition (better/normal appreciation) I think it's a fairly safe deal looking at the long term, assuming infrastructure around you continues to support the idea of renting it.

Major cities where STRs have only began rising up and gaining public spotlight with the rise of AirBNB are more likely to have more shifting and less stable regulatory environments since those areas are still in the process of trying to find the balance for STRs within their markets. 

Buying an out of state rental property from a realtor, wholesaler or off facebook or zillow etc as opposed to from an operation or turnkey provider who has an active, substancial, and effective boots on the ground team or teams to support you after you close on the sale. 

Here’s the situation (personal details removed):The tenant reached out explaining that they’re going through financial difficulties due to an ongoing divorce and lack of child support.

Investors don't have teeth, the loans that are GSE/FHA/USDA.. are supported by Federal funds intended to help owner occupants. 

I don't like one-time fees for software (he also says you can't buy it without signing up for his mentor/coaching program) because as a one-shot deal support, updates etc are usually pretty poor. 

Their debts would include not just car payments, student loans, and credit card payments but also things like child support paid.

I support (and use) a utility-cost cap amendment in our leases to ward off those who might want to mine cryptocurrency or operate an indoor greenhouse, but the vast majority of MTR have utilities included and the vast majority of travelers expect that they are.