Similar to buildium itself, once you set it up how you want it, it works seamlessly and helps keep a paper trail of move in's, periodic inspections, and move outs. 

It definitely doesn't seem as easy as on paper.

You get a piece of paper letting you know your lien was released, aaaaaaaand then you cash-out refinance.Can you not get an eighth loan but conventional 30-year fixed? 

You can also drive or walk a neighborhood and look for poorly maintained homes and find the owner that way (this method heavily depends on your market)  it probably wouldn't work to well in places like CA

Any other paper trail?  

In reality, I’ll be able to rent out one of the two units, and I will live in the other unit with a few friends, so I’ll actually be living for free & positively cash flowing, with a good cushion for potential issues/disasters, but I know that’s not how it’ll appear on paper unfortunately. 

However, with a realtor the house will be sold at a higher price, which brings in more cash.The concern with option 2 is that, if we do settle for the 75k offer that is  36% from the appraised price, which does not sit to well with us.

If I have a negative cashflow on paper or IRL this year, will I decrease my taxable income from my full time job?

That gives you can idea of how long they want to hold the paper for.

The Tenants kids spill koolaid ( poor people love koolaid ) and they let it sit or try to clean it up themselves by a wet towel instead of immediately using a steam cleaner .