Bottom line is that I’d rather keep the ability to use more than one password whenever it feels necessary, which is echoed by others in this thread. I also sometimes use 7-Zip for encryption in email when I know the recipient doesn’t have AxCrypt installed and would find it a burden to be asked. Yes, there are people like that!
Many people just aren’t “into” this stuff and that’s hard to explain to a programmer who’s steeped in it. For example, my elderly mom is barely aware that she’s even got AxCrypt and my sister only vaguely cares (I put it on both their machines via TeamViewer). When needed every few months, I send mom emails with an .axx file and “open with old-timer code” as an inside clue she can remember. But I don’t want that code to be the same one I use, and she will literally refuse to use a sharing code feature. Computer-phobic to a ridiculous degree.
So, the ability to make passwords on the fly (and still retain a master password) would get people like me on board with 2.0+. If feasible, you could have an “revert to v1 functionality” toggle. With that, I could get used to the new windowed GUI, which I do find superior to most of what’s out there.