Heck, what's wrong with keeping a separate gmail account (with the https setting enabled) for your purchases? IMO, if LE is snooping around, a site like safemail or hushmail is a lot more suspect (and sites like them have been busted in the past). Plus billions of emails each day get sent through something like gmail or yahoo.
I don't use any of those safe mail systems. Most are run by feds.
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Do bigger online stores/vendors have compatibility with PGP? I was under the assumption that both sender and reader had to each have the key to work. Would you have any tutorials or instructions on hand to add PGP to a standard online email (Gmail, Yahoo, etc?)