BOOM. There it is.
I would wager that this is the issue.
The computer does get left on and generally only restarted for updates. Which are usually about once a month, however I can guarantee that it has been restarted multiple times since April in fact I did an update a few weeks back, so I would suggest that the session data you are seeing at your end is definitely incorrect.
Just generalising here as I don't know how your handshaking and authentication is set up but mismatched session data could definitely cause the issues I have been seeing.
I would also bet that April is when I changed licenses. The dates I can see from initial email communication are back In May, but these are only responses, the issue was reported and initially experienced prior to this.
Regarding how often my computer is restarted - this should be irrelevant. Server side session data should be cleared down every time that the app contacts the server for initial authentication. This is basically every time the app is opened - i.e. every session.
The app itself is used very now and then. It is not left open when it is not in use, but does get left open for the duration of whatever I'm working on simply as it take an age to launch.
Generally after crashes I have to reauthenticate. (log in using my credentials).
I cannot recall if I need to do this when opening the app normally. (just checked - no).
However having just closed the app and then reopened it what I noted is that OSX went through it's application authentication process. This implies that the app checksum has changed i.e. it has been updated. Not sure of this is relevant but it should not happen in normal use, only on initial use.
Despite using the app I haven't had any more crashes over the weekend. I'll post here when the next one happens.