I don't know the arragement you have with your family friend, but if you don't bring cash to the table, it is going to take A LOT of successful flips to keep you housed, fed, and clothed, unless your friend wants to run a charity.I have a full-time mechanical engineering job in a chemical plant.

I doubt I"ll ever allow myself to really retire.I'm a mechanical engineer by education and work in the commercial utility business (power plants). 

Tip:  when thinking about your evential exit remember, the best time to plant oak trees is 20 years ago.

Would it help if you posted a few dozen videos about local things there in York, like a video tour of the Harley plant or maybe a interview with the owners of the Brogue country store?

Hello Anthony Carrasquillo, you can do all that was mentioned above and you may be forced to buy the property that no one wants...like the "fire damaged house" I found in Plant City last month.

I am a local with a family, so I'm planted, and am currently a wage slave (which also helps finance) looking for financial freedom. 

"The best time to plant a tree was 20 years ago.

I'm military and am about to plant some roots in Texas. 

I work a very demanding full time plant job that hopefully within the next couple of years I'll be able to leave and focus full time on investing.

You are on a solid path but planting additional ideas to ponder.