I'd buy a good saw & extra blades, a big axe, GB hatchet, costing about $100 total. Then for knives, I'd probably get a SAK Swiss champ, a Dozier slim outdoorsman or maybe a Lonewolf Loveless clippoint or something similar, BK&T patrol machete and some sharpening stones.
There are so many different carry preferences I have, that if you asked me the same question tomorrow, I'd buy something entirely different.
My ideal (more than $500) carry would be:
GB hatchet,
Dozier SO or a Tor or Raven from Ragweed,
Lonewolf loveless or Buxton custom,
big Busse, Fehrman, SR, Fallkniven, BK&T, CS, etc.
SAK
As I have said before, I would want to cover all bases, rather than only have one knife.
Come to think about it, for $200-$300 you could get a small Chainsaw, another $100 gas, and leave enough to buy a bucksaw for backup, and a few inexpensive knives ($100 buys a sh!tload of Moras)
This sounds like a pretty good thread to me, as it keeps me thinking about options.