Doing general paint and carpet cleaning for this property along with some minor repairs, junk removal and fixed a couple small plumbing issues (mostly deferred maintenance).

https://www.singlekey.com/en-us/ - I believe they screen the tenant as part of their underwriting before issuing the rent guarantee policy and the tenant also pays the premiums. 

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

I can however relatively quickly add up to a 500 Sqft garage.

Give fair housing testers the right to secretly record your call, trying to trap in a fair housing issue.

- The current low rent is probably to offset maintenance issues at the property.- Try to raise the rent and the tenant will give you a list of all the maintenance issues they want you to fix. --- They will offer to fix them in exchange for lower rent, but ask yourself, if the tenant has been living there for 25 years, why isn't everything fixed already?

I do not understand your remark as related to the DSCR loan.  2 ADUs are not allowed by f/f conventional financing but is not always enforced.Fortunately if you stay with the current tenant without a refi, by the time you pay principle it is likely the rent will have increased enough to absorb the increase mortgage payment. 

I don't care if I'm ahead or behind of anyone else because my goals are not relative to anyone else's progress.I get your point that staying active keeps your skills sharp and that if you're active when others aren't you will have access to opportunities that they do not.

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

I have been at this since 2021 so I am relatively new myself and really enjoyed it.