What needed to save in move from 8.6 to 9.2.2 and new HD?

I'm installing a new 40G HD in my 266 iMac with OS 8.6. I was going to burn the files and applications I want to keep to a disc, then move them over after I install 9.2.2 on the new drive.
Most of the applications and data files I use are on my desktop. Do I simply copy those, or are there related files in the System folder that I need to bring over as well? I know most applications will create new Preferences, but where would I find things like drivers for my printer, scanner and Zip drive?
Also, I know I need to put whatever OS I need on the first, <8G partition if I partition my HD, but is partitioning necessary? Once I have 9.2.2 up and running, can I install 10.3.x without any partitioning or other HD prep? Thanks.

wacoguy, data files are fine but whether you can copy applications depends entirely on the individual application, so you might like to list yours.
Many apps don't and some do install auxilliary files in the System Folder, and won't run without them. Of those many do and some don't give the auxilliary files names that make them easy for a User to identify and copy.
That aside, many apps that run in Mac OS 8 will be perfectly happy in OS 9; some need updating and a few will just give up. the same is true for the drivers and perhaps auxilliary utilities for your prniter and scanner, though I think a Zip drive should work natively with OS 9.
For all these reasons, even if the new drive was destined to have the same OS version the normal thing would be either to install everything afresh, or to copy everything from the old drive and then run updaters.
Copying everything from an old drive isn't recommended by Apple and frankly, if a problem arises, so what? You have a new drive with copies and can either wipe it all out and start afresh anyway, or just revert back to the old drive with the original files - either way, you lose only a bit of time…
Some people don't like partitions and personally I love them, particularly on machines that have only one real physical disk.
If you partition your disk you just get flexibility, with no apparent downside. You can use one partition as a back-up, use one to experiment with exactly this kind of major reconfiguration you're facing now, reconfigure one for particular projects and what have you…
If I was in your shoes I'd love to have partitions - then I could leave a factory-fresh System Folder on one and safely copy it to another, then play mix-and-match with the copy and my old files.
Each time I made safe progress adding one application or installing the printer, scanner or what-have-you, I'd copy the latest version to third partition so each time a change went wrong, I could wipe out any- or everything on the suspect partitioin and copy back the latest back-up… but some people don't like partitions.

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