I can see how it's not for everyone but personally I love being able to customise the bejeesus out of things. but once I'd had a glimpse of Foobar I just couldn't go back.

I didn't dislike MusicBee for what it's worth, and it looks and feels a lot like iTunes (only from several versions ago before some of Apple's more questionable design changes. The other things that constantly bugs me is how inconsistent it can be with the tagging sometimes - I'll spend ages carefully making sure tags are correct and then randomly a few weeks later it's decided that a random individual song from an album is actually on a different album with exactly the same details, and merging the two back together can be a total nightmare! My main irritations with iTunes are how slow it is - at one stage I wanted to be able to keep my Music on my server and point iTunes at it, but it's performance is totally atrocious for that (and to be honest even when the files are all local).

I'm not bothered if the application I go with can directly sync with the iPods, so long as there's some way of syncing the too - I don't really do it very often maybe change my gym playlist once every few months and sync my big iPod every half a year or so when I might have a significant amount of new music. I did see MediaMonkey as well, but was put off by the free/pro model they were using.

Musicbee ipod