Disclaimer: I have absolutely ZERO knowledge about the finances of this place, so keep that in mind for context. I am not speaking in any official manner whatsoever and I have no additional knowledge beyond what every user here has. I am speaking as a user here, not as a moderator and not in any official capacity.
The general impression that I get is that in the old days we made a fair chunk of change. Exactly how much I have no idea, but we were definitely worth keeping around financially. These days, with the decline of message boards in general, I think we’re barely keeping the lights on. Again, I have no knowledge of the finances here, but I suspect that paid memberships don’t bring in enough cash to get us up out of the “barely keeping the lights on” region of the finances. It would help, sure, but it’s not enough to turn is into the cash cow that we once were.
If I’m right, the financial managers of this place are being asked to fork over a bunch of cash to pay the software folks to implement a bunch of stuff that, if we’re lucky, might just barely make back more money than they invest into it (our old subscription software was strongly based around a vBulletin plugin which doesn’t work on Discourse for obvious reasons, so all of that needs to be redone). Message boards in general have long been in decline and if we’re not so lucky then they won’t make back their investment at all. That type of thing is a tough sell to management and might explain why they haven’t bothered with us.
I suspect that the real money was in advertising on the main page and the page views that came from new content, which we no longer have.
Again, just wild guessing on my part.