Lots of options for you! Just remember it doesn't matter what type of bike you ride, skill is what you will need in order to keep up with your friends, not a 2 or 4 stroke, or orange or red, however I prefer orange and 4 myself ;)
You might be able to find a 2001 KTM 400 MXC, that might be a good all around bike in your budget. Otherwise look at the WR426 or DRZ 400. All great trail bikes, yet the KTM will shine at the track and the WR on the Hill climbs, but any 250 2 stroke set up for the woods would also be a good choice.
For example, friends RM 250 2001 has a fly wheel weight, extra large tank, taller gears, and suspension redone. If you can't find a KX, CR, or YZ set up for the woods then the KTM 250 MXC or EXC.
Have fun and pace yoursefl!