I haven’t used her but @Katie Lepore has provided tons on insight on here and is also local to the San Diego area.

I have documentation of payments and evidence he lives here and a rental agreement.

Based off experience can you provide some recommendations on if this is a good idea and how to address his rent in this situation?  

This investor was from out of town, so I provided information about the area and performed multiple virtual showings making sure to point out the good, bad and ugly of each home.

You'd have to provide more details for anyone to give you a helpful answer.

Suppose you are personally sued; during the discovery process, you must provide information on all of your income and assets (including your LLCs in any state (with or without anonymity).

Sometimes they just provide the details and you’ll have to dig to find out.

LOWER ENTRY PRICE – Older low-rise condos provide investors with the opportunity to enter the Miami real estate market at a relatively lower price point compared to newer luxury developments.

If you're not finding the bookkeeping process to be a drag, and you're really just looking for efficiency (and possibly some additional level of detail/transparency than what your PM provides?)

You post info, share info, provide value, and they will come.