The issue I see with your $500 allowance is that in some seasons they will definitely be seeing a big cost.

.❌ Emotional Stress – Handling tenant issues (especially late payments or evictions) can be stressful, especially if you live in the same building.Hiring a Property Manager in ChicagoPros of Hiring a Property Manager✅ Less Stress & Time Commitment – A property manager handles everything from finding tenants to collecting rent and coordinating repairs.

are you handy or do you have team of handyman when issues arise?

If you want to message me your email address, I would be more than happy to send you what I have. 

It's usually the member/borrower's creditworthiness that is the issue and interferes with approval, not the LLC. 

I am on the Neighborhood Building Owner's Alliance weekly calls, and we had this ADU issue come up.

Quote from @Tommy Hardin: Have the issues with the REsimpli logo showing up in Esign been resolved?

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

This is because DSCR loans do not follow/ pass consumer protection laws. when you live in the property, it creates massive problems for this loan type and the lender which would issue it to you. 

If you tell someone too early you aren't renewing their lease, especially one who is aggressive, could lead you to issues.