@John Postma We are working with about 5 owners that are at the same stage as you with almost identical stories.

Quote from @Jim Crockett: Had a power couple go over to their ship despite my warning, they are young, we are not.

My question is if we are marketing this as land, is more value added from the 2020 mobile home or the multiple utility hook ups?

We just gave our tenants notice that we are planning to move into the rental they are leasing from us.  

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.

It's a commentary on those who take breaks because of market dynamics or because their buy box is too tight for the current market.

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

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?

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

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.