Hold them responsible and ensure they carry insurance.Now, with all those "layers" you can consider an LLC.

I don't think TRUST is the appropriate vehicle - - consider an LLC or S-Corp

I've told them it's a seller's market right now and most houses in our area are being sold between 1 wk and 1 month after going on the market, so if this house has been for sale longer than that (it has) and he hasn't had any offers (given the condition and location, I'm assuming not--I'm looking to use it for Section 8), he should really consider an investor's offer.  

Fannie Mae is refusing to consider an offer in 'as-is' and is adamant about making repairs before listing it.

Happens all the time in my market, feel free rerun your numbers and make sure you're not being too optimistic anywhere, but I don't typically consider an appraiser's opinion too highly, especially in a market that I know well. 

I would consider an FHA over conventional if it had an appraisal gap and they offered to pay for any FHA required inspection items.

Coverage for detatched Structures may be needed if you have any outbuildingsOptional Property coverages that you may need are:  Water Backup & Ordinance & LawFor Liability coverage, buy the most the company offers ($500,000 or $1,000,000) and consider an Umbrella policy to give additional coverage if the Liability coverage of the primary policy is exhausted.There will be other coverages that you should get depending on the properties, location, etc. and a good agent can discuss those with you

., so would consider an exception.  

consider an Uncle a "related person" ?

Consider an inexpensive domain leading prospective residents to a free WordPress site where you can control the reviews, the content and even list your available properties for rent/sale.