The problem of not being able to upload from iPod to the computer is bigger than sharing music with buddies. I have a couple friends who have 20 GB ipods, but only 6 - 10 GBs on their PCs. So each had much more music -- burned from their own disc collections -- on their iPods than their computers. One guy had his iPod stolen, another had it completely die. Both left with having to reburn 400 albums. Shitty. And they did that (along with introducing the 40 GB at the same price as my 20 GB) just months after I bought my 'state of the art' player.
I've never had a problem with my very old, classic 20 GB, and I love it. But Apple does suck about some things (then again, all big manufacturers/developers do...). One issue -- changing the iPod connections so that, if I get a new one, I need all new wires, car kits, travel kits, etc. SHITTY.
Meanwhile, I'm 50% ready to buy the 60 GB. I'm one of those who wants my whole collection with me...I listen to albums mostly, and never know what my mood will be.