Install OS X Panther. You'll need it for the new versions of Photoshop CS.
Backup everything to an external drive. Then disconnect all peripherals, do an "Erase and Install", DO checkmark "Install OS 9 Disk Drivers".
Be sure you have the maximum amount of RAM your machine will hold, or that you can afford.
Be COMMITTED to updating/upgrading everything to OS X and working in OS X exclusively. I still have OS 9 for classic on both my machines, but haven't used Classic, (OS 9) in more than a year.
Be COMMITTED to making the switch totally, in order to avoid confusing yourself, and creating lots of frustrations when something created in OS X won't print in OS 9 or vice-versa.
Jaguar 10.2.8 is rock solid, provided you don't try to muck it up with lots of third-party hackies and stuff. Remember to install that stuff, one-thing-at-a-time, so if something goes belly up, you can remove it.
From the looks of it, everything you have...including the SCSI Burner should work perfectly in OS X, provided you have the OS X software that recognizes the drive. Do the scanners rely on an Extension folder driver?? Have you gone to the website to see if they have OS X updaters?? (you CAN scan in OS 9 Classic, then switch back to OS X, but, its going to be a lot easier if you assure yourself that you have all the OS X compliant Photoshop plug-ins for acquiring images. (this assumes you are using Photoshop 7.01, of course).
The reason you are nervous is that, you are unsure you have covered all the bases.
If you need to walk through this, please feel free to write me off-list, and I'll try to do some long-distance confidence-building and help you make this transition. Its what I do. (among other stuff)
Clive gave you good advice....make sure your external backup is bootable.
Bill
Anyone have any advice....?
I have just placed an order for the Photoshop CS upgrade, and now have a week or so before it ships to instal OSX on my G4 450DP, which is currently running OS 9.2.2 I've installed OSX on a new out-of-the-box Powerbook before, but I'm very nervous about installing it onto my three-year-old main workhorse which runs two scanners, three external hard drives, a SCSI external CD writer, a printer, an Airport base station and generally works pretty smoothly day in, day out.
Bill Martin's Creative Services Macintosh Systems Administrator Consulting/Networking services and support OS 9.x, X 10.x.x
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