In my experience since time is money, I always hire out this initial process and have professional who does this regularly conduct a thorough feasibility study to tell me what's the best route to get me the biggest bang on a particular lot, look at Density allowances, etc. 

A section 8 tenant is mostly the same as a regular tenant, and your options to ask them to vacate shouldn't differ much.

All the same rules and steps of a regular flip apply. 

In my part of the country we see properties regularly selling for significantly over asking price with little to no contingencies.

That's why house hack BRRRRing only really works with a reno loan or a regular owner-occupied loan and then refinance after a year or two after making some upgrades. 

My wife is an Airbnb host so we’re probably not a good fit for your multi family project.

Hi Stephen, I host one here in the south loop.

Would I do a short term lease agreement or the regular lease that I use for the person only staying for the short term?  

@AJ H.Attorney and Title Company, would those be different than a regular lawyer?

Our agreement was he pays as much as he can and Up to half of the 1020 a month as regularly due!