Leverage REP status to use other losses against capital gains in the liquid assets of the company (invested in EFT's, etc)The policy for loss distribution would be:-All must be active (preferably material) participants to get deductions; hence the 20 or fewer so relationships can be maintained-Non-REP's can take up to $25k/y as PAL.

Which is what I prefer until I get my feet wet.

But, I spoke with another investor in the area that prefers short term, Airbnb rentals and is finding a lot of success doing that.

In general with house-hacking I'll always prefer small multi-families because it bakes diversification and efficiency into the purchase, giving you slightly more levers to pull and security in the investment. 

We prefer the equity when we sell, so I don't mind your scenario above.....with one exception that @Steve Vaughan brought forward."

I would also be the one responsible for the mortgage so I'm nervous about partnering up and would honestly prefer to do it myself.

One thing you could do that might really benefit you, is to find a small business coach (preferably one that knows the food/drink industry). 

Any other ideas as I'm looking for short or long term tenants, preferably short term. 

I am struggling with how to calculate school tax and property tax when I am analyzing properties and am not sure if there is a preferred method in figuring this out?

Which flooring do you prefer?