It is probably worth your time to connect with BOTH @John Warren and myself since we are both managing brokers, but John is more focused on property management and I am more focused on general contracting, but we are both Chicago investors as well.Oak Park and Lawndale are definitely two different markets.

4) does protest work because we are still part of bigger 25 years

We are based in Long Island NY but invest in the Mid-West. 

We are going to give it a try, but if we choose to either STR the property a bit with some personal use OR live in the property either some STR in 2025, does that trigger recapture or is it only on sale?

Complaints are being filed and we are resolving the matter via the appropriate channels. 

Ensure you have an itemized invoice from the cleaner, which can help justify the deduction.Reasonable Deductions: Long-term tenants often leave normal wear and tear, so I recommend being lenient on minor issues.

We are extremely unhappy with our property management company.

We are accredited investors and real estate brokers, and we are in our 70's, and we live in Maui.

We are in 11 markets, including Huntsville and would be happy to set up a call to talk over some options. 

We are in the Tampa, FL area.