I have a Powerbook 1.5 with 512RAM 80GB hard disk - and a HD5H.
It worked fine for me but was a bit of a pain in that I only had 20GB of hard disk available on my MAC.
What I did was:
1. Install Virtual PC
2. Install Win XP
3. Install SS 3.2
4. Went into my MAC iTunes directory structure and copied a 5GB 'chunk' of music onto the C: drive of my Virtual XP machine. This is due to the space restriction on my MAC. This process was a lengthy one.....maybe an hour? I forget now as I'd go and do something else! When I looked at the imported files using Win Explorer it seemed to convert the end parts of the track names to hexidecimal?
5. Started SS 3.2 and got it to pick up the 5GB of mp3's - which sorted everything out perfectly from iTunes, etc - no problems with the filenames.
6. Connect the HD5H to the USB drive
7. Transfer music to the player...this was particularly slow - I let it run overnight.
8. Once the mp3's were on the player I would then delete the mp3's from the C:\ drive of my virtual xp pc to free up more space.
9. I repeated steps 4 through to 8 until I had pulled all my music (25GB) out of iTunes.
10. Finally - I removed Bill Gates' pile of s**t from my Powerbook.....
Tip - make sure you edit all your music, genre info, etc correctly in iTunes first as it is a serious pain to have to do it once it's on the player i.e it's very slow!
My friend has his HD3 using SS 3.2 on his PC laptop and is forever updating his player....something which I don't do, but as my entire collection is now on there I'm not bothered. I may in a few months reload it all when I have a bit more music to put on, so I guess I've lost a bit of flexibility/functionality....
I use MP3's as they are universal - although not as good as ATRAC in quality for the size, I find that MP3's at 192 offer a good balance between both ie. size and quality.