From some of the things you've said, it sounds like your Windows File Associations for GSAK may be corrupted. You don't say which version of Windows you're running, but mentioned clicking the "Associate" button in GSAK - that will only work on Windows Vista or later if you are running GSAK as an administrator. If the problem recurs, you may want to right click on the GSAK icon, choose "Run as administrator" and then click the "Associate" button under Tools>File Associations to see if that sorts things out.
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