The majority of people are no more capable of GnuPG than understanding why RAM can't be solely used on a computer.
GnuPG has some weird defaults that are difficult to change as well without some command line commands. Ultimately your system will have a major flaw: passwords are typically have low entropy, and anyone with the same password will read the same mail unless you concatenate a salt the user has to remember. The ideal system would be to use Tor in conjunction with guerrillamail. Or to use a preshared key with a block cipher, and hide the encryption (since evidently you want to avert the attention of the NSA to be encrypting in the first place) using steganography.
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