Which lens for Canon DSLR?

I just picked up a Canon T1i which came with the 18-55mm IS lens. I want to purchase a telephoto zoom lens, but being a new to the hobby (and on a budget) I want to dip my toes in the pool first before jumping all the way in. Basically, I'm wanting to spend less than $200.

I understand that what makes great pictures is great glass, but the fact of the matter is I don't have $500 + to drop on a lens. Therefore, which lenses would you experts recommend? Here are some of the lenses that are in my price range. I've read reviews on each of them, but as with everything, the reviews range widely. Any insight you guys can give would be appreciated!

Canon EF-S 55-250mm f/4-5.6 IS Autofocus Avg $250, but I can find it a little cheaper
Canon Zoom Telephoto EF 75-300mm f/4.0-5.6 III Autofocus - DC motor avg $160
Canon Zoom Telephoto EF 75-300mm f/4.0-5.6 III USM Autofocus - USM motor avg $190
Sigma 50-200mm f/4-5.6 DC OS HSM Avg $160, has image stabilization, but is only 200mm
Sigma Zoom Telephoto 70-300mm f/4-5.6 DG Macro Avg $160, has macro function
Tamron Zoom Telephoto AF 75-300mm f/4.0-5.6 LD Macro Avg $125, has macro function
Tamron Zoom Telephoto AF 70-300mm f/4-5.6 Di LD Macro Avg $165, has macro function

Regarding the Canons, from what I understand the USM version of this lens still uses a gear drive and while technically it's a USM it's really not the same as the USM versions in the L series. Therefore, is it really worth the extra $30 over the DC motor? Also, the 55-250 has the IS feature. Will this feature be worth it to go with a lens that only goes to 250mm as opposed to the other two which go to 300mm? I will be shooting some wakeboarding shots, so I suppose I need to be able to zoom in on a rider riding 75 ft out.

Lastly, I've read good and bad things about 3rd party lenses such as the ones from Sigma and Tamron. The question is, which category do the ones I've listed above fall into?