I know we all got to make a living but....

He lives locally, is very responsive.

I buy and hold and do short term rentals and mid term rentals.Located in Racine Wisconsin  Hello Gabriel: I also live in Racine County there are some great deals our way and including southern milwaukee county too!   

Those that own it can be harder to sell as the cash flow from the business will cover the debt service for the business, but not for the real estate.Example: I had a very high-end assisted living facility on the market. 

The St Germain Act states that state governments can NOT outlaw due on sale clauses except for transfers from an individual to a revocable living trust.

We haven't lived in the townhouse in the last 2/5 years so we would get hit with full capital gains.

If they do, you may have a chance under the scenario you're proposing - if they share your concern for it's condition (although that seems unlikely since they've been living with it the way it is for some time, it seems).If you own it, it's pretty lowbrow to expect a neighbor to invest in your property. 

U live a lifestyle not a job huge difference..

Live off of equity as you sell or live off cashflow.

A little about me for context: I live in a very expensive market in Rye,NY.