iTunes (Windows) is very easy to set up and use for it's most basic functions, on a single ipod and single computer. I have found it very hard to figure out how to do non-standard things, such as move a database from built-in drive to external drive, and have it be recognized, OR, to manage multiple iPods with drastically differing capacity.
Some people have experience iTunes as easy to use, I think because they have stuck to the most basic functions.
I would not describe it as overall very badly designed; just designed with an extremely heavy bias to the most basic functionality. It does offer the power user more headaches than should be required.
