You can blame all the thieves for this. Yes, sharing paid for fonts and software has forced companies to go the subscription route. It's either that or shut down. I didn't like it at first either since I was one that would wait two or three versions before upgrading. But I always bought my software. Hacked and cracked software was killing many companies.
I partly agree with this. I've always been one that believe if someone delivered a quality product, they should be compensated. That even goes for open source software that I use (which I use a lot more of nowadays then I used to).
However, bare in mind that CC was cracked not long after rollout. I think it's easier to sell to the masses that line of thinking, but I feel that it's more about generating a consistent revenue stream, as you said yourself, you didn't upgrade as often. I would stipulate that it's more about having a constant revenue stream on mature software.
I actually did upgrade every iteration and I actually paid full price (I didn't like how they handled the upgrade policy back in the old days, so it was worth it to me to buy outright every iteration).
However, the subscription model means paying more for less control over what you are buying. That I don't like at all.
Thankfully, I can use legacy software without affecting me like some. I don't get proprietary formats sent to me, even if I did, plenty of open source programs to view them (as when I get the files, most people just want me to replicate them and my process is the same regardless if it's a vector or raster file (which this is what I get 98% of the time)). If I'm creating the files, then I can use whatever I want. Not everyone has that luxury I know.
How do you keep improving your software and adding features if people aren't going to purchase the upgrades.
There will always be a need for upgrades for nothing else to support newer standards and/or hardware. No way around that.
My need to buy most of the software that I use for business is usually because of a need for newer hardware support and/or standards that people are using. Other features, such as toolsets, I use the same ones that I've been using just about since I started in this trade (some were added later, but all tools that I use now have been well established in the various software packages that I use). Mainly because I was always swapping software and these were tools that were consistent among them and provided the greatest ability of control.
I was pissed at first when Adobe went subscription, but what I pay per year isn't much more than keeping my two main programs updated with the latest features, plus I get access to their entire suite which include all their fonts plus cloud storage. So I'm learning Muse and Dreamweaver and will be adding web design to my list of services. I consider it the cost of doing business and I pay way more per month for a lot of other services that are also necessary for running a sign shop. Many of our own have brought this on ourselves.
If one only uses 1 or 2 programs or if one uses the entire suite, then it's dealer choice. If you need quite a few programs, but not all, then it actually costs more over the years and that is including upgrading each version using the perpetual license method as well. Bare in mind too, one is subject to price hikes or changes in the policy and really doesn't have much recourse unless going somewhere else or start back using a legacy version. Essentially doing something else.
You also have to remember (and this is just me), I don't like having production rigs connected to the internet. Which one has to have when using cloud services and at least a few times to verify subscription on locally installed programs that require that. I believe that does more harm then good. Not only at the individual software level, but also how MS is handling their OS now.