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

Anyways- if it were you, would you go ahead and redo the kitchen with new cabinets/granite, and put in new windows - or would you leave them as is - and spruce up the kitchen with a coat of paint to the cabinets as a temporary update , and just wait 5-10 years when it's time to sell to do those type of upgrades/rehab (New windows and New kitchen).

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.

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).

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

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

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?)

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.

Hey @Regina Bailey - If for some reason you didn't get the Chicago lease from others above feel free to reach out to me and I can provide it.

The latter seems to provide a middle ground that could enable professional maintenance oversight while allowing me to retain some control, mainly through tenant communication and management portals like RentRedi.