Afraid to upgrade

Hi there,

I've been putting off upgrading from 10.5.8 for a long time. Actually that's not quite true. My HD failed and i had to buy and install a new one. On the new one I installed 10.6 and then what i think I did is a recovery from a backup. When i restarted i was back on 10.5.8. Not sure why that happened.

Anyway last night i got a grey apple logo and a spinning wheel. After trying various things she rebooted. i immedietly did a backup and then also ran 'CleanMyMac' and it's now running great again.

I recently bought an ipod touch 5th gen and i can't connect it to iTunes as I can't upgrade beyond Itunes 10.6.3 using os10.5.8. SO, again i'm thinking it's time to go to snow leopard. My snow leopard is on usb. My main reason for not upgrading is the state my computer is in. Years of files not filed very well. 3 or 4 folders called 'Sort'. I always planned to sit down one weekend and sort all my files, but it never happens.

So do you think I can upgrade but maintain my files in their dishevelled state? If so, does anyone know the option i need to select when doing the install? Or do I just need to sort my files properly and do a full install and then transfer wanted files, re-import emails / addresses / calendar items and re-install softwares?

regards, Graham.