I'm okay with the ripping and tagging process, though thanks for bringing up another method that I hadn't considered. I was really wondering what the capabilities of the Laguna's MP3 player are. It seems that they can be very variable between devices.
For ripping, I've always used Audiograbber, so I'll probably stick with it: I even bought it back in the days when it was shareware rather than freeware (I think the author gave in to pressure from similar freeware apps.) I do have another suite of apps for sorting out 'problem discs' that refuse to play in the Clio thanks to copy protection (I've paid for the music, so I expect to be able to listen to it in the car, thanks very much!
Audiograbber links to Lame and FreeDB quite nicely - just insert your disc, click the FreeDB button to load all of the album details (assuming that it's recognised - I've found one or two that weren't) and it'll rip and encode to MP3 on the fly and populate both ID3 V1 and V2 tags from the FreeDB data. It even gives good control of the file structure (I like the folders to be in the format 'Artist - title' and the tracks to be named 'Track no. - Track title.') There's also a handy feature that lets you set the start and end points on a track. Pointless most of the time, but really handy when someone thinks it's clever to add 20 minutes of silence and then 10 seconds of jibberish onto the end of the final track.
For mass re-tagging of MP3s, I haven't found anything better than ID3TagIt. It can be a bit flaky (especially if you delete the folder that it's currently looking at) but otherwise does a sensible job. It can rename files, or even re-organise the directory structure of your entire MP3 collection based on the ID3 tags. It can also create ID3 tags based on the filename (useful in conjunction with Audiograbber if you want to rip via WAV for some reason.)
I've already got the discs, so I think I might just burn out a couple of RW's and see how it goes. I can see it's going to be a bit of trial and error, but if I'm using rewritable discs, then it's not like it's costing me anything other than time, is it?