Working this backwards, what I see is a 3rd party trying to benefit from another’s house via rental cashflow, My only business is 30+ years as probate estate and trust lending in CA.

A property allowing one-night stays may be more prone to fraternity parties and similar.

It's not hard to understand the disqualified party rules and prohibited transactions. 

While they’re out partying, you’ll be home learning, analyzing deals, and honing your craft.

After several hearings, we reached an agreement: both parties agreed that if the tenants applied for government assistance to cover the overdue rent and committed to paying rent on time going forward, the eviction process would end.

Quote from @Ryan Konen: You are correct that comping software like Privy, Propwire, and Propstream primarily rely on public records for their data, such as county assessor records, MLS feeds, and sometimes 3rd party aggregators.

Post Dodd Frank sellers have continued the same bad practice of selling houses to occupants with financing at selling prices that are way high, can't be justified via any type of 3rd party valuation (appraisal, zestimate, tax value, even recent sales in the same area).   

Be mindful of a gift tax implications if you sell a house for less than FMV.Also be mindful of transactions between related parties when selling at a loss.

The owner, the lender or a third party? 

Looking for help and suggestions- I want to say I have learned my lesson and now know to use a third party to hold funds.This is my first time working with a private lender/family member.