Some people like to keep systems they know - often having spent years living with it. Other's like to keep as up to date as they can - they must have whatever is new.
When I started with PC's, I ran CP/M but also had a second CPU to run a new DOS system in case it took off. If I could ever afford a hard disk, I could choose between a capacity of 5 or 10 MBs (not GBs). How times change.
Software doesn't change quite as fast. Within a few years, I had settled on major tools I still prefer to use a decade or two later. Sadly some other tools are no longer available. They were often very good, but for various reasons, the market chose inferior products and the technology the good products used died. There were some serious anti-competitive tricks in some cases, but for whatever reason people tend to settle for "average" - and I believe we all pay the price.
Today the business model is going through another significant change. Software is now sold on a subscription basis. It has many issues to be aware of - it can be convenient not having to buy software, but two issues come to mind.
First is control of language leads to control of thoughts. It's hard not imagine George Orwell saying "I told you" if he saw today's world.
Second is even small amounts can be prohibitive for some. Many third world countries have escaped the PC and now use their phones.
We are caught up in an issue I for one did not appreciate. A few people last updated their accounting software when the GST rate changed. We don't need to update accounting software quite as often as suppliers like - I believe three years is the optimum (can be pushed a little although support usually runs out at three years). Following the cloud, even new desktop software from most suppliers is only licensed for a year. Naturally suppliers like the subscription model better - and at least it stops people expecting support well beyond a reasonable time frame.
However, I've recently discovered that Windows 10 (early versions) is no longer supported by some programs that were previously fine. It hasn't affected accounting systems yet as far as I know, but we all need to be aware of the fact that when a system "supports Windows 10", it may well be limited to more current versions of Windows 10.