I'm just going to write a few items I think you should consider, you can combine them in any way you want. I'm shooting Nikon, so no suggestions for Canon. Here it goes:
A used Nikon D200 is about USD700. Sure, the D300 is much better, and with it's ISO performance can make many average lenses into fast lenses, but think about the price difference and if it's worth it for you.
The Tamron 17-50mm f/2.8 is a very good lens as many already mentioned, and has a very good price perfomance ratio at about USD350.
The Sigma 70-200mm f/2.8 ships at around USD850 here, and is a very good standard telephoto lens, although maybe too short for sports or wildlife.
For macro and portraits, a Macro (or Micro...) lens in the 90~105mm range from Sigma, Tamron or Tokina will deliver good performance at a reasonable price.
Hope it helps.