In most markets owning a B&B is a lifestyle choice.

Quote from @Bill B.: Ps.

If a renter wants to extend for a few months their stay beyond the initial lease term, will I be a) required to extend and b) at the same rate as their existing rate?

Our market is very heavy tourists, so a lot of individually owned STR condos, but honestly I've personally have had more success in long-term rentals doing the BRRRR strategy with small multi-families and B-Class SFR's. 

We could work backwards from the condo's upper tier pricing (that you would likely get into contract at) and backwards calculate how much income you're going to need to qualify given the probability of how the rest of your rental income and liabilities will be caluclated.We do these calculations (plan A, B, C, etc) on a daily basis.

I'm curious where the line is drawn b/c I can write off a meal when I am leaving my 9-5 job and going straight to a volleyball match to officiate (second job). 

We focus mainly on value add properties in A/B areas.

If it helps, I live in Philly and am thinking about B Class areas- SFH & MF properties.

Will be above a 1.2 DSCR and LTV will be between 50 and 60% on a good B class rental.

Those that claim to cashflow well are either a) full of it or b) old and in a class C area where your probability of being able to achieve those cashflows are low.