You'd need to put a bit more thought into that, at least to start thinking in more detailed terms than "US" and "outside".
Countries, visa types, schools for your kid, work opportunities for your wife, local language, acceptance of your identity (believe me, majority of places in the world are much worse in that regard than Trump could ever be), etc, etc....
What I can promise you is that money situation will be worse. Uprooting yourself and moving somewhere is a costly endeavor (did that 2 times, it's not fun), and besides that US is the best country to earn money out there, it's much harder to cover necessities and have disposable income pretty much anywhere else.
Encryption in transit is pretty much solved these days with TLS, what OP wants is E2E - encryption from sender to recipient with no intermediate parties having an idea about contents of the message. Problem with E2E is inconvenience: emails are inaccessible without private keys and key management is pain. Users don't want additional headache of managing their keys between bajillion of devices where they might use emails