For $300, you could do pretty well with the 50mm f1.8 and the 28-105mm f3.5-4.5 USM. Since you said that you aren't too big into landscapes, you won't miss the wide end too much, and the extra reach is always nice to have. I have both, and they are pretty decent lenses. They aren't L quality by any stretch of the imagination, but i think that put together they would suit your use pretty well. Since you seem to be all over the place with what you want to shoot, I wouldn't get anything too specific to start with. If you want to do some macro stuff, pick up some extension tubes. It's cheaper than a macro lens, and you can use them with different lenses.
----Brad---- 


