Check with your lender to make sure they are comfortable lending with this period of 3-6 months where your cashflow is light.In terms of updates and tenants, it sounds like you may have time to complete them at the end of each lease expiration.

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.

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?)

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.

Based on the information provided, it seems like this could be a solid long-term investment opportunity.

Open escrow with homeowner, end-buyer, and self; self transfers contract to purchase to end-buyer in Title/Escrow, and provides T/E with end-buyer's contract with self: agreement to purchase, and fee instructions for self ($10k + difference if any) to be paid out of closing escrow5.

Transferring to a LLC provides you fake protection (note I am not an attorney but have common sense).

I work on a local team that provides free educational classes on investing and I am happy to help you with any local connections I have that may be helpful to you in your journey!