I alsodidn't see any mention of HOA fees/dues and or rules.

for double closing you would need your funds to buy then sell it to end buyer at premium. there are transactional funding companies that can lend the cash for a fee.

In order to encourage tenants to get renter's insurance, we have been contemplating instituting a $50 monthly fee until they provide proof of renter's insurance with the owner listed as an additional insured, but not sure how well that would hold up if we ever had to evict. 

With DSTs you need to make sure that the various fees don’t negate your profits.

If I could start finding off market deals myself I think it could work, usually the assignment fee from wholesalers is the difference between pulling all your money out and not.   

Also there is a management fee to pay for all of the above.

Offer discounts for applying in a short time period or- offer a free application fee. 

If you’ve considered a cost seg study in the past but they were too expensive, times have changed and the fees have gone down significantly.

There are consulting companies who do this (for a fee) and i can also share some contacts if you need some. 

If he opts for a townhouse, a low HOA fee will help his buying power It gets tricky using lease agreement income when purchasing a house so I do not think that idea will work.