A better upgrade system will definitely be a big win in my book. I finally upgraded from Vista to 7 a couple of weeks ago, and the process took about 4-5 hours. The first try, it actually did not work properly, so I had to start over from the beginning. Fortunately, my old Vista installation was still in tact at the time, so it went smoothly after that.
Sounds good. Upgrade straight off the net sounds a bit scary but I expect they will download all the source files before the upgrade wipes the hardware drivers and attempts to reinstall network connectivity. Don't fancy a semi-bricked box or the bad publicity that could cause.