Got my big new hard drives in hand - Now, what don't I know?

Got my big new hard drives in hand - Now what?
Have 2 old iMacs that I need to upgrade with bigger HDD’s and then upgrade the OS. I am experienced with hard and software upgrades since MacSE days (got all the tutorials marked) but not so much with recent OS10 permutations. Certain that all this has been posted here numerous times, but quite tired of searching for it after a couple hours and have probably unnecessarilly confused and frightened myself in sorting through the scary posts. Perhaps its all in an FAQ at another site?
1. M9290LL/A G4 iMac 20” 1.25 Ghz 2GB RAM OS10.3.9
2. M9845LL/A G5 iMac 20” ALS 2.0 Ghz 2GB RAM OS10.4.11
Presuming that I would clean up the existing internal HDDs, install the new drives (1TB & 500GB) in their appropriate external enclosures, initialize them with the apropriate HFS (know I saw that here somewhere), drag and drop the existing internal HDD onto the new external drive, boot from the external HDD for an appropriate test period (all 5 family users) and only then install the new drives in the iMacs.
With the files and user settings safely backed up on the old HDDs in the external enclosures, I can safely attempt OS upgrading. Already have family packs of newer OS versions, just never desired the weeklong headache of reconfigging 5 users and the typical screaming lost settings sessions.
I am not looking at a clean system and software install because of all the user settings. We have a fortune in legacy PowerPC software, some of which never worked right on the G5 with 10.4, but Safari for 10.3 is now very unstable and I have printers with no 10.3 drivers available.
Questions:
1.What should I do to clean up the existing HDDs prior to copying over besides running Disk Utility. Didn’t Disk Utility. used to include a de-frag function? Hopefully there is shareware and this doesn’t require a $100 software suite.
2. Do I need special cloning software due to windows-like traps in OS10 or can I just copy the entire old drive, sludge and all?
3.What are the ultimate OS10 versions for these machines;
at what point am I installing lots of Intel code that simply slows these machines down or kludges up the legacy software?
4. What else did I forget to ask? What would the pros at my local mac shop charge me fortune to do?
Thanks

The prevailing answer to my posts is that I should either attempt a clean install and migration over using SD to clone copy the existing internal drive.
How good is the current migration experience? I've been doing OS upgrades since Mac SE days and never had a clean one in my life. Always lost the whole email folder or all the bookmarks or the address book files or the entire iTunes library or something that resulted in long hours of cursing and frustration. And that was with a single user.
And I know that these units will boot and be functional with upgrades to 10.4 and/or10.5. Unanswered is whether these computers will work faster or slower and more or less reliably?
Am not concerned with OS9 apps; have a couple old CRT iMac doorstops if the kids are overcome with a wave of nostalgia for Marathon or Pod Racer.
Does this or any other site maintain a master list of 10.4 / 10.5 software version compatibilty, or do I have to track down 50 different vendors' current websites?

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