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Security is definitely a hurdle, but I don't think it's insurmountable.

The main benefit to using Attachcache is greater automation. It sounds like you're doing work to get your attachments filed away. All that opening, closing, context switching adds up over time.

With Attachcache, you can either set up a Gmail "has:attachment" filter to be used in conjunction with Forwarding, or just use Sync. After you've done one of those 2 things, it's a totally hands-free solution:

https://mail.google.com/support/bin/answer.py?answer=7190

Also, Attachcache Sync is retroactive -- it can mirror my 2k+ emails and 8k+ attachments going back to 2006 in about 10 minutes. Doing this by hand would take a long time.

Hope that explanation helps, and thanks a lot for your comment!