I LOVE my iPod, and I wouldn't want someone to not use it becasue of crappy Windows apps. My reaction at first was that MM 7.50.5002 (version on the new iPod cd) needed a lot of help. After working with tech support for a few days, I was given a new version to install. The "new" version has an older build number, but I'm told really is a newer build. I installed 7.50.3103 the other night, and I havne't had any problems with it since. It syncs in a matter of seconds for few changes, or minutes for whole albulm rips. I haven't heard back from MM tech support as to if this version is readily available.
I don't know why Apple would take a great device and pair it with inferior software. In one way I guess it points out how good iTunes is, but at the same time it is obviously frustrating/discouraging new iPod owners.
Give 7.50.3103 a shot before you make any final decisions.