I wish that I had seen this sooner... I have a slingbox and I use Shaw Extreme. Actually the only reason that I upgrades to Extreme a few months ago was to increase my upload from 0.5 Mbps to 1 Mbps.
The bottleneck is definitely your upload speed. At 0.5 Mbps, the picture is pretty bad but tolerable for "regular" TV shows. Sports is horrendous, unfortunately, until you get up into 1 Mbps territory. Even then, sometimes the clock is hard to read because it is blocky, but at least you can follow the play around a bit. Definitely great when you're in a pinch, but at the expense of quality.
If there was a way to halve my download speed and double my upload speed for the same price, I'd do it simply for slingboxing and VPN-ing into my home computer.
You can also view your Slingbox over your own local network, and the quality is quite good. I only have the Slingbox Solo (non-HD), but I can get speeds of about 6 Mbps locally, which makes for a nice, clear picture. Better than standard-def cable, for sure. I'll often stream things to my second monitor while I'm at my computer, or to my iPhone while I'm around the house. My laptops can be used as little TVs if I want them to.
Let me know if you've got any more questions about the Slingbox and I'll try my best to answer. And if you want to preview what it looks like on a 1 Mbps upload connection, I'm sure that I could let you log in and have a look. As long as you don't order any pron PPV. Haha.
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