How to save/reinstall 9.2 iTunes, programs, when switching to Tiger?

Hi, fellow Macphiles!
I've got some serious questions about switching to Tiger. I hope some of you can help me!
For starters, I've been extremely reluctant to switch to OS X - period. I've been pretty comfy with OS 9.2 for a long time. But, alas, looks like the time's come to switch to not only a new computer, but Tiger, as well. So, here goes!
1. I have over 3 GB of iTunes on my computer. I'd like to save them and then transfer them to iTunes on the new computer I plan on getting (I'd be, of course, using the iTunes program that comes w/Tiger). How would I do that to make sure they work with Tiger's iTunes program? I don't have any huge Zip discs or anything major save 3 GB's of anything to.
2. I have Adobe Photoshop on my current computer. How would I save it and the transfer that program to a new Mac? Just put it on disc and then install it on the new Mac?
3. I've been using Outlook Express as my email client. How would I save my messages and other things in OE to transfer to Tiger? I really want to save these things but don't know exactly how I'd work that.
4. I have other things, also - pix, documents, AppleWorks documents, MS Word .... would I only have to save those all to a disc and then reinstall on the new computer?
5. What about saving my many Netscape bookmarks and transferring them to a new 'puter and Tiger? Possible?
-- please help, if you can. I don't want to lose everything I've put on my computer over the last 5 years in a big computer/OS switch-over. If I can't exactly figure this out, I'm going to have to stay 9.2, and I'd rather not, especially since there aren't any good or useful downloads out there anymore for 9.2's. Besides, I can't use a muchly-coveted iPod with 9.2. iPods are calling my name (another reason I don't want to lose my iTunes in a switchover)! Thanks guys!
iMac - G3 Mac OS 9.2.x

Welcome to the Discussions, Princess!
Switching from OS 9 to OS X will involve manually moving your files from your old computer via CD-R, external hard drive, or target disk mode. If your iMac G3 cannot burn disks, then the CD-R option is out; if no Firewire port on your iMac G3, then target disk mode is also out. Therefore, your options are external hard drive or network sharing.
Assuming that you are going to get a new Mac with an Intel processor, you need to be aware of various Application types:
OS 9 (Classic): these will not operate on a new Intel Mac
OS X (PowerPC): these will operate, but are not optimized for an Intel Mac
OS X (Universal): these operate, and are optimized, for both Intel and PowerPC
Without knowing exactly which versions of the Applications that you have, it is difficult to guess which category they fall into. The good news is that there are OS X versions of AppleWorks and Photoshop, and obviously iTunes. If you move your iTunes music to your new Mac, then it will probably be recognizable or importable by iTunes. Your email may be more of an issue, but many programs will import old mail including Apple's own Mail program. A new Mac comes with many other programs such as iPhoto, which overlaps some of Photoshop's capabilities. If you know where your bookmark file is, it can be imported into Safari.
Take it slow, and by all means ask more questions as you go.
Good Luck!
bd

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