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I would get an XR 250 or something along those lines. What u really want is a bike with enough power to get u up and down steep hills and over big logs. if this is your first bike than don't worry about its looks too much because you will be bound to dump it a few times.
when looking at bikes make shure they start/ run well and bring your mechanic friend along to look at the bike. check EVERYTHING! look at the frame for dents/ missing chunks, check the bearings, chain, sprockets, breaks, spokes, suspension, compression, tread left on tires, and the clutch. you want a bike that will be as reliable as the day it was bought from the dealer.
Dirt bikes are a ton of fun in the woods, espically if you have your own land to make trails in. If only i was closer to where you live then we could ride together and make some bomb trails : )