[mahyarm]

Don't use PGP! It's cumbersome and difficult to use with other people easily. It doesn't give you forward secrecy or deniability. Use OTR and have it always on, any client that has implemented OTR will turn it on automatically. Use passworded archives to encrypt file sets, it's something most computers and users understand.

[jlgreco]

Do chat clients fall back to non-OTR when the other client doesn't support it? As I recall there are some chat clients that have an "OTR" feature that really just turns off logging. I imagine it being quite the hassle getting the other person working with it.

[joelhooks]

Adium does this, optionally. It is configurable. It is occasionally a PITA, but usually "just works"