Can't help you with the first part and my answer to the 2nd part might be a little out of your price range but here goes. I brought a Creative Zen in Feb last year and love it. Although I had a few problems with the software this has now all been sorted with the new (free) organiser from Creative and it has made it a truly seamless experience syncing between the pc and the player. The CD ripper that comes with the software also seems to work well as does the tagger.
Like you I could not justify the price of the Ipod and the recent news about their battery life adds another nail to their coffin.
Have seen that prices for the new Zen NX 30gb version have dropped below what I paid for my old one at £250 (doh!), but that is technology for you.
You might find the following website useful for prices (check on hard disk players).
http://www.advancedmp3players.co.uk/...tem/index.html