drmoze said:
I'm old-ish too (almost 50!) and I would suggest the Sony HD5 (or HD5H) as an option. Especially if you just want to rip your own CD collection, and if you have live or classical music. The Sony (using Atrac formats) will play back gaplessly. The HD5 is wonderfully small with a huge battery life. So you can have lots of music with you and not worry about frequent recharging.
SonicStage is fine once you get it installed and running. Just rip, rip, rip, then transfer to the player. After I got by a few initial glitches, it has been very easy to rip the rest of my CDs and transfer songs to the player. If the Atrac3+ encoding at 64kbps sounds good to you (it does to me), then you can carry a *lot* of music in your player! (Almost 1000 CDs or so.)
iTunes is a bit nicer interface, but once the player is loaded up, that doesn't matter as much. The Sony is great for taking with you everywhere and listening with no battery worries.
I second this.
If you care anything for Sound, which is what the player is used for, then go for Sony. There are no gaps in between the song when you use Atrac compression, which means that songs that merge into each other play seamlessly and properly like a cd player. The sound is alot better than its competitions but you will want to get a decent set of headphones, as with any player you buy these days.
HD5 is 20 gig, HD5H is 30 gig.
You should use software as it helps you to organise your music. And there is nothing wrong with Sonicstage, the software that comes with the Sony HD5, it is easier to use than iTunes (iPods software).
Navigation is simple with the buttons, and the dedicated volume buttons are very handy.
The battery lasts much longer, arguably double the length of the iPod. and its removable so if you plan on keeping it for a long time you can buy spare batteries and replace it yourself without having to send the whole unit in to the company to get it replaced.
With Atrac3+ 64kbps you can fit twice as many of your CDs in the same amount of space and still have the same sound quality.
If you want any other info on the HD5 just ask...