And this means you're going to spend some money on that person.

And you can't legally dictate how much they carry for personal belongings. 

Personally, I like to target 30% equity retention in each deal.- Section 8 income isn't guaranteed.

Quote from @Michael Challenger: I have no qualms with hard money lending, but I need to learn more about the process and structure to these for typical deals so that I am more comfortable and in a position to reduce my personal risk and risk to investors as much as possible.

I personally think this is the direction booking sites need to go.

I personally use Bnbcalc: https://bnbcalc.com/?

I don't have a solution but I think a real estate attorney or a title attorney would be a good person to talk to.

Referrals from local investors on BiggerPockets can be a great resource. https://www.biggerpockets.com/business/finder/agents@Mark Ainley sounds like a great person to link up with!

What made you think this person had no experience whatsoever and didn't own their own home? 

Advanced QuickBooks ProAdvisor was introduced in 2007, to get certified the requirement was: one had to be certified for 3 years in a row and had to attend 2 day in person and online courses.