This is a really good post @Alan Asriants , and we've honestly experienced some of the struggles while growing our general contracting business here in Chicago.It is REALLY HARD to manage subcontractors - period. 

A lot of the success with voucher tenants really comes down to treating it like a structured program, not just “guaranteed rent.”One of the biggest lessons many owners learn early is that the inspection standards matter.

What guarantee the LL will timely and fairly issue a refund?

The LLC (very likely) has zero credit, assets etc so you as the owner of the LLC will still give a personal guarantee and the loan pricing will be based on your personal credit score.  

DSCR loans will have a waiting period after bankruptcy generally speaking.

What is the best way I can jump in by getting 2 land loans in a short period of time?

When making my first offer, I noticed that there was not an attorney review period in my contract.

Hey BP fam,
Section 8 gets a lot of mixed reviews, but if you screen voucher tenants just as strictly as market-rate ones, it’s a massive cash-flow stabilizer.
Here is why leaning into the voucher program is a solid...

What you’re really trying to determine is income stability and documentation consistency, not just gross deposits.A few things many landlords look for:Two years of tax returns (Schedule C if sole proprietor) to verify reported incomeYear-to-date profit & loss statementConsistency of deposits over time, not just one strong monthBusiness license (if applicable)Length of time in businessWith self-employed applicants, I usually focus more on:Income trend (steady vs volatile)Cash reservesRental history and payment consistencyIf half the income is cash deposits, that’s not automatically disqualifying in trades like painting, but you’d want to see that it’s been consistent over a longer period and aligns with reported income.The key isn’t to reject self-employed applicants — it’s to apply a structured, consistent standard for verifying stability.

Back when I didn’t have assets worth defending, I was more than willing to provide my personal guarantee to make a deal happen, or to get better loan terms.