I prefer the cleaners coming closer to the time of the next guest than immediately after the last guest leaves (normally this is only an issue during our slower season).  

Start by normal DD and circle back eventually? 

Which is basically just reported on your schedule E/C and taxed just as normal.  

Typically a cost seg can provide a ton of benefits to accelerate depreciation on pieces of the purchase that wouldn't usually be allocated out under normal circumstances. 

My personal soapbox statement - Airbnb is an abusive spouse that slowly people are waking up to realize they are in a controling abusive relationship and they start to develop an escape plan (more platforms/direct website) so they are no longer relying on Airbnb.

Based on previous deals through this wholesaler I can average out wholesaler normal up charge percentage.

There is a level of participate required when you buy a business and a piece of property.While it always depends, on average, acquiring a business will normally require more work.

The happiest time for me developing locations is when we hit 65% on our first buildings which is normally our Cash flow breakeven point. 

4. what all more is involved with Section 8 tenant than a normal tenant moving in from paperwork or procedure point of view?

Maybe a house hack/live in flip.I'm not aware of your markets normal appreciation though, so do take that into consideration.