Many owners are retired and on a fixed income and can't afford the charges, so they're forced to sell.I want to help them stay in their home, while forcing equity for myself.Of course there will be due diligence on the building to make sure the rent can cover what the actual costs will be, including future assessments (being a manager, I do this for my clients) and make sure the owner / tenant can actually afford that rent.What am I missing?

There are plenty of examples of people who have lost their jobs and were forced to make something work in order to support their families.

Short sales usually require a hardship letter to the lender explaining your hardship (job loss, death in the family, forced relocation, divorce, medical bills), your lack of assets and your lack of income.

My bet is that he won't voluntarily leave and you'll be forced to evict him.

(Click on the "learn" tab above) One of the more interesting points he made was that on a multi-family, you can force appreciation.

If you're going the forced appreciation route you aren't getting your 30k back.

You may be forced to use a non-traditional lender (ie: not a major bank).  

You’d likely have to get involved in task force initiatives, block clubs, community groups, get police involvement etc.  

Without going into detail, we were forced to "mutually terminate" our agreement after it took him 12 months to get the foundation and utilities in.We purchased our land in October 2016 outright for $107000 and got a construction loan for $320000 in May 2017.

Although my Broker didn't do everything correct by standing behind its agent, and it is seriously in dereliction of asserting its rights to include its agent in negotiation, Opcity's fault lies in bait and switch the agents coming in by its website, and not showing the referral fee on the Opcity-Agent Agreement, and forcefully demanding 35% based on a referral fee schedule not suitable for NYC market.