Wow. I really wanted to love Mediamonkey. Actually I do love Mediamonkey because it’s a damn fine piece of software. There are some warts like the fact that the newest version, 3.0, has a link to the Yahoo Podcast directory when that service was discontinued back in October of 2007. That is a minor thing though.
The biggest wart, and the reason I can’t use the software, is the iPod syncing. It “works” but there are glitches all of the time like artwork not being set properly for albums (I had Benny Goodman looking out at me from a Telemann piece for instance). The iPod “fast scroll” feature where you get the letter of the alphabet pop up when you are scanning quickly through the playlist doesn’t work right because for whatever reason when Mediamonkey syncs it isn’t making the iPod ignore “The” in band names. I get no indication that the iTunes-purchased song I just synced won’t actually play back on the iPod. It will play back just fine in Mediamonkey itself however.
So, even with all of the great features that Mediamonkey has, I’m heading back to iTunes simply because it works better with my iPod and that is just more important to me because my music collection isn’t big enough to bog down iTunes. If the Mediamonkey guys could fix that stuff I’d pay for it in a heartbeat but that day hasn’t arrived yet 😉