I just finished the first pass. I went through all the files I currently have, trying to come as close as possible to the original tapes for J and also catering to my brother's taste in music. My iTunes has over 3700 files. That's less than meets the ear: There's a large chunk of Shockwave material in various forms, and almost all the music is in at least two forms: uncompressed for burning on CD and compressed for an iPod. This has given me the impetus to clean up a lot of my iTunes files, the majority of which were imported from previously digitized files. The names and other annotation is not part of most of them, and I've been having a grand time fixing iTunes listings. Whee!
The easy part is done. The file for the DVD is up to 708 songs, 1.6 days of music, only 2.65 gigs. I can put several hundred more songs on, and probably will. The hard part is coming: Adding as many of the songs to iTunes. I have to compare my lists of the tapes with the songs already on file, then find the CD and add the tracks. One CD is not a big deal; dozens of them might be.
I'm just sort of amused that I'll wind up with a collection of perhaps a thousand songs -- ones that I rate highly -- mainly for kids/tweens/young teens but not exclusively so, on a DVD that cannot be played: You MUST go through iTunes (or the equivalent) and listen digitally. I now have a lot more kids music on CD than I did ten years ago, and while I won't be able to find every song from a tape, my bro will like the collection.
The second tape has This Island Earth by Dandelion Wine. Time to import music...