If it were me, knowing everything that I know now, and knowing how I like to ride:
KLR650 or DR650. Budget about $5,000 here. Ride it everywhere, use it as a DD/vacation bike
Some sort of sportbike/ Sport-touring bike. Think VFR800, SV1000, 1250 Bandit. Something comfortable enough, good handling, good power, ability to carry luggage.
That would put you under budget easily. I would consider a true 'dirt bike' or a sportster for a third, but that would depend on your riding area. A smaller dual sport would make a good third bike also, say a DR350, WR250, KLX250, etc.
Just my .02