>For example, I would consider PGP encryption (with due >diligence) as an
intelligence grade *tactical* security >measure. But for intelligence grade
*strategical* security, >I would again encrypt it, but treat it as if it
still is in >plain text, and take additional precautions accordingly.
How does encrypting something twice transform it from tactical to strategic?
It sounds like both of these are tactics/methods.
Strategic security would be taking into account different components and
coming up with a set of cohesive tactics to achieve security under a specific
threat model, including MITM attacks and physical attacks (which would make
double or multiple encryption useless).
Frankly, I'm skeptical that anyone would benefit from this kind of
conversation, or that anyone here could (or should) provide useful advise
beyond what you qualify as "Commercial grade tactical security." Mandatory
cartoon: https://www.xkcd.com/538/
If you truly want privacy in your communications and you are not a computer
security expert, better go for a walk in the park/woods with your
coconspirator(s). You'll get the added benefit of fresh air.