Try reinstalling Quicken 2008 after uninstalling it first via 'Add/Remove Programs" in Control Panel. this should help.
Also check out THIS
article on converting Quicken files to new versions and other info..It may prove to be quite useful..
As for the IBM Laptop not recognizing the flash drive, generally they come with a driver CD. Try installing that on the IBM and see. If you do not have the CD, you should be able to find the driver from the manufacturer's website, or do a google.
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