If you go that route, you'll need a survey anyway so factor that into your costs.

There is another factor at play for me, though.

I work 8 hours a day plus about an extra two hours of driving, one hour to work and one hour back.

I scour for MLS listings each day to see if any good opportunities pop up and I'm also slowly training my mother and sister to drive for dollars.

I don't think $30-40k in cap gains will matter much to you tax bill, depending on your w-2 income.Over the last couple years I have been amazed at how little taxes are a factor when I report $70k in gains/yr or less. 

That’s my dilemma, the historic value is definitely a factor, who doesn’t think a house built in 1780 isn’t cool.

I'm just in Asheville for the VA right now because I have multiple issues from Iraq, including a brain injury which currently prevents me from driving. 

It is key to have a driving vision.

I do it all the time when I'm cooking, washing dishes, driving, etc.

That most professionals who are Entrepreneurs understand that building your business means you need to Drive it like a Car.