May I ask why you use lossless on a portable player?
On topic/
My music library is almost 80gigs. I snyc about 22 gigs of music and the rest are TV shows and my apps (which are around 2 gigs). I can't believe I thought about getting the 16gb phone again. So glad I got the 32.
Because I sometimes like to listen to music on my Shure 530SEs (especially on the train, since they're sound isolating). Compression artifacts are much more noticeable on high fidelity headphones.
And as a side note, I've always kept space to under 1GB, across all 3 gens. I haven't ever seen a performance hit, though in fairness, I only have them over 1GB free while experimenting looking for the differences. Also, itunes recently added an option to fill all your free space with random songs- not a move I would expect them to make if "too full" lead to decreased performance.