What you've described in your question is a clearly prohibited transaction.

Financing this will come down to two things (in my opinion): the self sufficiency calc (3-4 unit FHA requirement - property must be self-sustaining) and finding comps to evaluate it for appraisal. (2)Does anyone know of a property similar to the one I have described?

Can anyone describe where to at least start?

My cousin had a commercial loan ("blanket mortgage") such as described in option #4 above. 

What I am doing is developing a platform where the seller, in the situation you just described, is able to find and hire an hourly or fixed priced expert who actually went through a similar situation a number of times before and can advise the seller.

Here at BP, the term for what you're describing is called "house hacking".

@Alan Grobmeier,  Unfortunately, even if @Eric DeVito could do a 1031 (which he can't because it's his primary)  it would not work the way you describe.  

I'm looking for a small multi at the moment, but if I see something like you described in the heights I'll keep you in mind.

When I graduated from high school, I stuck the middle finger up at college and started working with my dad. 7 years later I cant describe how thankful I am to have made that decision, and the support system that I had that many young investors don't get from their families.I was sent to Las Vegas in 2012 to manage rentals and construction of the 100+ units that we bought in 2012.

I'm not too good at describing this so I might mix up the terms a little bit but you should be able to get the idea of what I'm asking.