If you're intending to rip a few hundred hours of speech, that sounds like a few hundred CD's. A small flash memory player probably won't cut it then. A hard disk player sounds like the way to go. There are new mini-HD players that supposedly hold around 2GB, but I have no experience with them.
From what I've seen, the HDD based players (Apple IPOD, Creative Nomad, etc) allow better organization of songs since they have full LCD screens instead of the small info displays on the flash-based players.
As far as software, I use Poikosoft's Easy CD-DA 5.0 to rip. It's free at download.com for a trial version. The quality can be set as low as 8kbit/s; I don't know if you can turn down the frequency from 44khz. I'd just play around with it, and look for the happy medium between file size abd quality.
I'd search download.com for "CD ripper" or "audio encoder" or "audio converter" programs. There are lots of free demo versions of the software that will allow you to see all the features of a particular program.
Once you've got a general idea of the number and sizes of the files you'll be playing, it should become clearer as to how much capacity you need.