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Don't get a lensbaby, I bought one a ways back for artsy shit, thats what it's made for, not sports. It allows you to manipulate the lens to give an odd dof in portions of the photograph. Kind of like a poorly made tilt-shift.
The 50mm f/1.8 is a waste of cash in my opinion. Yes it's under $100 and it produces great images if it's on a tripod, but the build is subpar with a completely plastic mount. And it's af is super slow and noisy so you'll miss most action shots unless pre-focused. If for portrait stuff though, go for it. You might want to look into the f/1.4 for a couple hundo more.
Telephotos, get an L series while you're still new, you won't regret it. The water sealing, build quality, and optics are amazing. If you don't care about the physical condition, you can get a 70-200 f/4 for under $500. $500-$550 would be if you wanted great condition. I use a 70-200 f/2.8 IS L, which allows for use in super dark places, and the IS helps a ton for low shutter speeds.
Just buy a 70-200 used and you won't regret your decision.
Yes, and trust me that jump in iso is very important with entry level cameras as they are super noisy even at 800 to begin with. I try and keep my iso at 50 in the day and 400 in the dark and play with the shutter speed. It's much more important than playing with the iso. Better to get a noisy shot, than a blurry unuseable shot.
I'd have to disagree/say you can't tell. I've done very close inspection on both lenses and can't tell a difference at a 3000% zoom. Unless you are saying the f/4 at f/4 is sharper than the f/2.8 at f/2.8, then I'd agree, it's due to the amount of bokeh produced. I can tell you that the f/2.8 is much sharper than it's counterpart the f/2.8 IS due to the extra elements and stabilizing unit.
I rarely shoot the f/2.8 at f/2.8 to be honest unless necessary, I normally bump it down to f/4 for better clarity when the shutter speed is not an issue. The f/2.8 lenss has a much better af than its counterpart the f/4 lens, which is the most important.