Punch List: Accounts for any punch list items involved. 

And there is a lot of appreciation potential.For someone just starting out, I'd suggest focusing on traditional long-term rentals before jumping into short-term rentals.

As expenses fluctuate (property taxes, insurance, maintenance items, etc), the cash flow is up and down and unreliable.

Do negotiation with the tenantIf it is item 2, what are the do’s and don’ts

These lenders often have more flexibility with underwriting and may not require traditional income documentation.

With it being a difficult property for an investor to find traditional financing for, how would I go about assigning a realistic valuation for the property if we were to entertain a sale?

While the traditional approach involves buying a multi family property, living in one unit and renting out the other - with rising prices and interest rates; others have considered renting out bedrooms as unit spaces. 

The idea is spreading, and could spread to some other spots here that have traditionally been STR friendly. 

-> Funding: you can consider as options mortage brokers who can scout/compare the best offers in the market and you can also consider public funding programmes that exists as an incentive to renovate and bring houses to the market, either for tourism or traditional rental.As an example, on the traditional rental there is a funding program ("Arrendamento Acessivel") that funds up to 90% of the project and can be used to cover part of the renovation costs, as well as, part of the purchasing.

.- The 203(k) will allow you to bid on properties that need repairs that won't qualify for a traditional mortgage => less competition => better purchase price.You will need to find a great local contractor you can trust to supply the required bids to qualify for the 203(k).- After closing, you can do some of the work yourself to save money, but the program doesn't allow you to pay yourself.You will want to buy a Class B property, maybe Class C+, in an area that seems to be improving.