The flashing question mark issue was one that I used to fix with Disk Warrior on a regular basis with OS 9. It always found small problems with the disk directory if I remember correctly. I've never had that problem with OS X.
I think if you used Disk Warrior on that TiBook it would fix the issue, but you might try giving
Alsoft a call and make sure the latest version of DW will boot up and run on it. I believe it will and it's a great utility, but I'd hate to have you buy it and find out it won't do the job due to the age of your setup. You could also find a friend who has a copy and go that route.
If you get it back up and running, definitely get the extra RAM and upgrade to at least OS X Panther or Tiger as artie505 suggests. You'll think you got a new machine with the kick both of those upgrades will add.
Also consider just using Classic if you need OS 9 unless there's a specific reason to boot into it. I bought my original MDD Power Mac so I could dual boot OS 9 and OS X on it, but once I got my feet wet with OS X I never looked back. Classic will run nearly everything you need it to, with the added benefit of keeping you in OS X most of the time and all of the goodness that brings.
