I know this may be simplifying things,  but isn't dealing with tenant problems and problem tenants what we hire a property manager for?  

I would need an under simplified scenario to offer any advice. 

Your plan seems to be over-simplified and has many holes in it.

It simplifies the CRM into categories for buyers and sellers, though its app is somewhat lacking.

To me it kind of simplifies things when you can move someone in for x number of months/ years and know you’ll have something consistent coming in.

Here’s a simplified breakdown:Lease Agreement: Since your buddy signed a 12-month lease in July '24, he is legally protected until the end of the lease term unless the lease has specific clauses allowing early termination under certain conditions.No New Lease Signed: Since no new lease was signed for the new home and no formal agreement was made, the original lease terms for the townhouse still apply.Landlord’s Request: If the landlord wants to break the lease or has changed their mind about the swap, they would typically need a valid reason, like a breach of lease terms, or might need to negotiate an agreement with your buddy (buy out)Legal Advice: Your buddy might consider consulting a local attorney or legal aid service for advice on his specific situation.

If the software is not simplifying your life or making you more accurate, you shouldn't use it.

Even when we try to simplify by going through County versus City, there are still nuances that you'll want to make sure you cover before you move on your decision.   

We can differentiate our offering by providing a simplified and easy start for guests.

Here are a few points to consider:Operating LLC (Y) Under Parent Holding LLC (X):Pros: Keeping Y under X might simplify your structure and reporting, as everything flows through the parent.