Tom:
I started out with a Personal Jukebox. 20gb. I got all my music on it and started ripping and coding books on CD from the Chicago Public Library. Filled it up fast, so I started saving the books on my external 250gb backup hard drive. I also got a 40gb iPod last year. The menu system for the iPod is just awful compared to the clear, simple menu system for the Jukebox. However, the iPod is smaller and easier to use when I'm biking. Also, and here's a huge problem, the Jukebox was designed to make it impossible to recover from its hard drive. The original thinking was that music was not supposed to be copied. I gave away my entire Cd collection after I transferred it to the Jukebox. I lucked into a UK website that reversed engineered the Jukebox, wrote new firmware that made it possible to transfer everything onto my hard drive. It took 24 hours to transfer everything, but I was glad I could do it. Now I have all my music on the iPod, plus about 30 books at a time. When I'm biking, I can choose, and I'm not lugging a heavy MP3 player. In fact I have given the Jukebox to my brother after loading their entire Cd collection on it. I also have their music backed up on my computer hard drive and on the backup drive, like my music.
Now, to the books. I have been working to rip and code every audio book on CD I can get (all fiction, 95% mysteries) from libraries for the past 3 or 4 years. In fact, this week I'm doing the 30 or so books that Mesa PL has acquired since last spring when I ripped and coded their collection. I have something like 215 books saved and another 15 to do from the main branch before I look at what's at the east side branch. They're all saved in MP3 format, and they load to the iPod in minutes. In fact, before I put my music collection on the iPod, I was able to cram 63 books on it, with the rest of the collection backed up.
My toad and my motorhome have only CD players, so I bought an FM transmitter that is compatible with the iPod. There are some compatible with other players, where they plug into the earphone jack. So I'm legal when I'm listening to books on the road. I also have some cupholder adapters coming from Amazon that will hole the iPod upright in either vehicle while it's playing. The FM transmitter works great, by the way. I was looking at a Belkin at Circuit City for my brother. $50. Some of them are lousy, so you need to read reviews on Amazon or someplace.
Earphones. I tried the Etymotic ER4P in-ear phones. They were VERY expensive. I think over $200. Unless they are very firmly and deeply inserted in the ear canal, the sound is tinny. For books that's not so important. What I found was that, despite a lot of ear cleaning, I was having trouble hearing, because they were jamming up my ears. So I gulped hard at the loss and did some research. Last weekend I picked up the Bang & Olufsen earphones. They are just fantastic. Great base, great music sound. I need something that doesn't crush over the top of my head under my biking helmet. These things cost around $170 and are extremely well made. I don't have much money, but I'm almost tempted to get a backup pair, because they are so perfect for my needs. Then, again, if they're that expensive, they should last, and I wouldn't want them if they didn't, I guess. The ones that came with the iPod are already staticky and worthless.
I bought some excellent Altec iPod speakers, but I gave them to my brother and sister-in-law, who are having a great time with them. They played them for a month on the same 4 AA batteries; the sound is superb; they have an auxiliary input jack for microphone (I think) and definitely for the Jukebox. In fact, they came with a short wire to go from the aux to the Jukebox's earphone jack. They have a dock for the iPod.
Since I have everybody's music and all the books backed up (music is double backed up), they can drop the Jukebox in a lake while fishing and I'll be able to whip everything onto a new MP3 player quickly.
Hope some of this is of interest. I really enjoy playing with this stuff. Copying the books is extremely boring, but it's time well spent. Each CD takes about 5 minutes, including loading, unloading, etc. Oh, by the way, I downloaded and use Musicmatch. I'm currently on Ver 10. $19.95. Works fine. I don't think iTunes rips and codes.
--pat