If you don't want to deal with appending random data in front of every
file you encrypt, you could just encrypt them twice (with different
passphrases each time of course).

Technically, no. There is a class of attacks called "Meet in the Middle" attacks. There is a reason why we don't use 2DES and go straight to 3DES (standard DES has a 56bit key, 3DES is equivalent to 112bits of key strength, with 3 56bit keys...). 3DES is slow to implement in software, thus creating the need for AES with larger key sizes.

A search on google will drop you a ton of links describing this attack.

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Public key available at pgp.mit.edu keyID:36F46FD0


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