Couple of suggestions:
For your "pole barn", look into a post and beam construction. (Or for that matter, just frame it like a house) Much better IMO, and something you and a couple of buddies could do yourselves. If you decide to do build it yourself, get an account at a local lumber yard vs the big box stores (I saved 20%+). You'll likely get better pricing, and better quality lumber.
I'd also consider buying all the materials yourself with the new found acct at the lumber yard, and that way you can write off the sales tax as major purchases. If you build both buildings, the sales tax alone might qualify you to itemize your deductions, plus medical, plus charitable, property taxes, license plates, etc etc. I'd also get my own building permit. That way, you can fire a contractor at will. If a builder pulls it, you're stuck with him for the entire process.
If you plan on clearing out any trees, I'd start removing every pine tree there is, and any sweet-gum trees. Both are dirty, shed needles or pods like dogs shed hair, and take a toll on your soil.
Just my 2¢.
