However they had a house go into foreclosure this year, declared bankruptcy, have no landlord references, currently lives with his mom and he's around 40 and had his money give me the deposit money.

Worst case scenario, you liquidate these assets, declare ACME LLC bankrupt, and everyone goes on their merry way. 

Ensure you are familiar with the Declaration and Bylaws of the specific Condo Association; I own a unit and the docs clearly state the Owner of the unit is accountable for all payments, penalties and fines, so I would never relegate paying the HOA to my Tenant.

I previously had a more normal type of slab leak on a different unit with more normal costs to fix (I think it was ~$3k total cost including water loss) and had not declared it against the insurance (but now wonder if I should have). 

Who is declaring this requirement?

I did get one potential lead from someone that may be declaring Bankruptcy.Good luck with your responses.

This becomes a chicken & egg discussion for me.Not to mention the fact that I'm not ready to declare, in perpetuity, that treasuries are "safe".The simple fact is, people will always need a place to live and there is no new land being created, unless you are in Japan or UAE, where they are pouring sand into the ocean!

Sure, it would be a learning experience for him, but declaring bankruptcy in your early 20's is an expensive way to learn.

Many people have a heart to invest in young men/women who are teachable and have hustle muscle!

So declaring all this subcontractor expense on your return without also having a bunch of 1099s logged on your account with the IRS is a pretty big red flag.