iTunes

I hate how you can't just drag and drop music files in your iPod. I recently had to reformat and the fact that you can't take music OUT of your iPod ( as far as I know ) , I had to re-download... Also it looks for the exact playlist you had before so even if you have all the songs on your iPod and it doesn't find the folder you originally synced it's going to erase and re-sync.

iTunes can suck it.

iTunes can /SMD