Could you explain what a house-hack deal is?

@Andrew PettittMy first advice would be to set your objectives down (near-, mid- & long-term) in bullet form and find yourself an accountant to lay out a plan to meet your current and future needs while mitigating taxable events along the way.Holding your properties in your personal name in the beginning is usually the best approach - you can deduct expenses against your income (even income from other sources).  

I even reviewed with him that the tax records say that the building is a SFH but he assured me that the town does not restrict use of lots to SFH/Multi/Commercial/Ect.The CEO is willing to write a letter explaining that to the appraiser that the transition from a SFH to a Multi-family was completed 20 years ago and there have been multiple town assessments sense that time.

Thanks for the reply and explaining!

This may happen maybe only once in 1,000 showings but, honestly how do you explain that to an owner?

For instance ours says basically:Buyer has X days to do inspection (lets say 7)Buyer has Y days to review reports (lets say 3)Buyer and seller have Z days (lets say 3) to come to a written agreement after objections are raised or either party can cancel.

But it wouldn't be fun to explain to the irs how you got cash from a sale but it really wasn't from the sale etc. 

@Clint CoonsWould you mind explaining how an S Corp avoids NIIT under your illustrated fact pattern if you don't extract taxable income from the corp as W-2 income?

It isn't the right thing to do to just lock the door, but sometimes explaining that as a licensee they have given up their tenant rights, helps get them out before you have to do it.

You'll just need to explain your living situation.