Your story and lifestyle  sound very interesting. 

If you're looking to retire in a few years and you want a simple zero hassle lifestyle perhaps a REIT or a solid stock/bond portfolio would be great.  

(get seller to pay the closing costs and you can get a decent house pretty cheap)The cons: -you will have to pay PMI for life of the loan- contractors that do the work need to have all proper paperwork, and lead cert if doing lead work (these guys can be a lot more expensive)- 3.5% is based on total project cost, not just the price you pay for the home.

So 2 questions :1) To tax my assignment fee properly what should I do?

Indianapolis isn't Hawaii Bob(stating the obvious)Even if a house does not appreciate for 20 yrs, and rents, only go up a few percent a year.If a property is bought right and cash flows properly.

Unless they made lifestyle changes and cut other monthly expenses, assistance in making their mortgage payments is not going to solve their problem.

She gave information regarding evictions and the proper process.

That would be a long-term speculative move.I do find it hard to believe that an 8-unit property isn't zoned properly.

I left the Chicagoland area (Chicago proper - not the 'burb dwellers who like to claim Chicago) and WISH that I had house-hacked while I was there.  

You will pay a little more (not much), but you will always get proper legal advice from them, advice that a title company can never give.