The property clearly needs some work done, roof & windows being the main two, but we know going in that we would have 20-25k to but into the building without feeling like we bought into a mistake deal. 

Maybe you could find a 200-300 from the budget and paint just the main spaces in the house also.

I'm mainly looking for cashflow,loan paydown,tax benefits,rather than appreciation.

The extender is located 30-40 feet from the main access point, and I think it almost has a line of sight.

Price should be in the $1,500-$2,500 range for the main service change.

My main focus right now is training and development. 

Is there one main employer in the region?

I haven’t made any moves yet well mainly because I’m from a small town and don’t know how to get started. 

The bulk of my time and energy drain on this one was finding hardwood to best match 60yr old soft fir 'hardwood' flooring, figuring out how to blend old asbestos tile siding patches with something modern and the main drain and in-wall dryer venting. 

One of the main reason the last recession took longer than it should to recover were people like you who saw success during the growth period and all of a sudden the recession hit with no contingency plan to keep your investment.