OS 10.5.8 Leopard. Recovering old data from Time Machine after HD replacement.

Okay, I have and iMac dual core Model A1224, EMC 2210, 20" screen, 2.66GHz processor, 2GB RAM, came, when I bought it, with a 500 GB drive circa late 2008. The drive started to fail about 2 weeks ago, random shut downs, wouldn't boot up, couldn't find the OS. Could sometime recover booting up from the original OS disk in the C drive, but eventually even that failed. Had run disk first aid and TechTool Pro6 to no avail, they all passed the drive so it was a mechanical failure,not bad sectors.
REPLACED the drive with a brand new Seagate Barracuda 1TB drive, figured I was all set, Time Machine had backed up the old drive every day since 2009 to an external 1TB drive. I could even see the data there. Now new drive is installed and I need to load the OS to it and retrieve my data from Time Machine. Put in the old disk, Leopard 10.5.1, and walked along and asked it to bring in the data from Time Machine.... except, the data is saved on Time Machine in a new version of Leopard, ver. 10.5.8 and so the 10.5.1 version can't import it, but of course Migration Assistant will allow you to import it later.
So, I continue to load the OS via the disk, then go to software update after creating a new computer name, which I didn't want to do. Updated the software so I am now running OS 10.5.8, open Migration Assistant and attempt to migrate / recover the old data from Time Machine. I can get some stuff, but it insists on my resetting everything up all over again, all new accounts in Quicken and Thunderbird and Microsoft Office, no recovery of data already there and I can't access the accounts that were set up by others, it indicates I don't have sufficient privileges though I was an Administrator on the old computer and on the current system as well.
Frankly, I need that old data, so how do I get it? Do I bite the bullet and upgrade the system to Snow Leopard OS10.6.XX, will that allow me access to old data under OS 10.5.8? Will it be backwards compatible? How about moving up to Lion? Would that be a better way to go and will I be able to recover that old data then?
VERY frustrated here! Thanks for help or direction you all can provide.

HI,
Have you looked through Pondini's extensive TM help site?
http://Pondini.org/TM/FAQ.html
http://pondini.org/TM/Troubleshooting.html
Can't imagine what he hasn't covered!

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    HI,
    Have you looked through Pondini's extensive TM help site?
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    http://pondini.org/TM/Troubleshooting.html
    Can't imagine what he hasn't covered!

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