You know, Im starting to get the impression that the thinking around here is a little, shall I say, blockchain centric.
An eepsite centralised but can host databases.
Absolutely under no circumstance should this system rely on any centralized service.
PGP is an additional step that I think would sink any attempts to make such a thing widely used
Encryption would be transparent to the user.
The hard work would be on the GUI
I have many years of programming experience using wxWidgets (among others).