Wildwest, I forgot about your disconnected preference as you have mentioned it many times before, that in and of itself is a reason they will probably always offer a perpetual license (even if they don't advertise its availability). I would assume a non-negligible portion of their market is still lacking reliable internet service, we were until a couple years ago.
This actually doesn't enter into my equation, but since you brought it up. Issues on your end or their end could present problems, even in areas of otherwise stable internet.
I also agree with most of your opinions about keeping things up to date, however, in my (somewhat limited) experience the most stable and reliable path has been to keep all computers,operating systems, software, and equipment as up to date as possible.
Updates, in of themselves are unstable. It is introducing unknown variables into a system. My experience with Win 10 (which is really just my dad's computers and he doesn't get the cheap components) has never been good with each and every major release. In fact, MS scrapped Oct.'s update due to they never got it right and now you have April's update, which has it's own issues. Win 10 is actually what made me switch to a totally different ecosystem (and while I don't run it on a production
computer, but a personal desktop, Manjaro (Arch based distro) has been far more stable then
Windows 10 has ever been and it's "bleeding edge" just like Win 10 is). And while not everyone can go that way, it's been far more stable then
Windows has ever been and I've been a
Windows user since I was in the single digits (back in the DOS days) and it's honestly put the fun back into using a desktop.
Windows has it's issues that run deep (especially considering it's legacy bloat) that affect both security (the fact that zero day's always keep coming up and they have been vulnerabilities since the 9x days) and stability of the system (at least in my non-coder's, but geeky
computer user's estimation).
The irony is, if a system isn't connected to the outside world, it doesn't need to be totally up to date. Just stable.
This is obviously a balance that requires financial consideration.
Add into the fact that each major Win 10 update goes EOL 18 months from when it was released (not when you get it, but when it's released) and since those are major feature updates, they can break programs or in order to take advantage of them, you have to keep up with the hardware (
computer) and software. That can also add into the need to keep up to date with those as well.
This all adds to the instability of everything, by the time a major Win 10 update gets stable for everyone (if it ever does (RE: Oct. '18 update never was fixed)), it's practically EOL.
Forced updates (at least with regard to the major feature updates) should not be done unless they can insure ultimate stability, which they certainly don't have that track record. I actually would have had sympathy for them (certainly more then I would with Apple and Apple doesn't always escape this (RE: initial release of High Sierra)), but not since they forced it.
Coming from an engineering background where every software has been moving the same direction for many years (to subscription licensing) I half expected it from the signage software.
I have no doubt that is the way that most closed source commercial software is going (main reason why I've gone totally open source with my entire workflow), and those that "have to" stick with those programs, I have sympathy for y'all, because when they go to raise those prices (and there is no ability to hold off until later), cost of doing business is going to only going to go higher.