If it's steady, your job is to make it more steady by spending to do the repairs and upgrades early, not late, and then capitalizing long-term on that in rent.

My agents comps showed the home being 260k-300k, and they were confident rent could be over 2400.

Lenders will want to verify this with monthly rental lease payments, utility bill, or a LOE from a relative if you live rent free. 

At $250/night (This is mostly a guess as to value of a VIP room) with 28 nights it would be 42.8 years to break even without accounting for inflation (today's dollars are worth more than tomorrow's dollars).Do you get any of the return from the room being rented out on the days other than the 28 days? 

With just the data given, I would say buy a duplex, rent out the other side, and if you have extra bedrooms in your unit, rent those too. 

Obviously, we need to maximize our tax effectiveness in the situation and the monthly is going to be huge, especially if we can’t get the rents to cover the mortgage.

How much is your current rent or cost to rent a similar property you are looking for?

This is the STR version of seeing what similar properties rent for on ZIllow. 

Greetings,This is likely a silly question, but are hard money lenders ever willing to fund 100% of a down payment on a large purchase (20+ units) after viewing the deal (rent rolls, etc)?

Rents together are $3400 each month.