[slovette]

While you are right in practice, your reasons are wrong. It’s not because these companies can’t afford it, as mentioned it’s actually cheaper. The part you referenced, about forced upgrading, is often more costly than simply having a subscription that routinely keeps the software updated. The problem is three fold:

1. Small businesses don’t upgrade because they fear change in general. Buttons disappearing, functionalities changing and new things like cloud integrations scare/confuse a lot of them. They also don’t want the pain of paying people for time to relearn what used to work just fine.

2. Subscription costs are very much more visible on P&L’s than one time expense charges. When the eventual tight times come, recurring costs are the first thing on the chopping block.

3. As you know, cutting most subs means cutting functionality as well. For small places like photography studios, they don’t want their core software to be beholden to a required recurring expense. They want to own it, so if all else goes away, at least it still gets the job done.

It’s often simplified to be a cost thing, but it almost never really is. They can afford it, but they don’t like what they give up in the model.

[benrbray]

I think people fear change in software because updates have a habit of making the user experience worse. Think of the troubling trend in web design where they take away customization options and add more padding to everything to be "mobile friendly".

[acdha]

This is a valid concern but your comment really highlights a big problem with these discussions: your wording implies that this is universally bad but your examples are both things where it's impossible to say whether a given move is a win, loss, or wash without fairly detailed data. An increasing percentage of people are either mobile-only or mobile-primary, so making things mobile/tablet friendly is probably a good idea for most sites. Similarly, customization has significant training and support costs and removing infrequently used features to add things more people care about is a classic business trade-off.

[fourthark]

There's no real reason for a customer to care about these trade offs. They want to get work done, nor worry about the business model behind one of their tools.

[acdha]

That's looking at the problem backwards: if you have one customer who has a bunch of customization requests you need to weigh their business against what other work you could be doing with the same development time. It's not a win if you keep one customer but lose others to a competitor whose product is easier to use or cheaper to develop, especially since I've probably seen at least a 1:10 ratio for arcane features and customizations which a customer swears up and down are mission critical to things which actually are — usually it's more like one guy doesn't want to consider changing the way he works in the slightest until forced.

[potta_coffee]

Adobe software became notably worse (IMO) shortly before they went to subscription model. I remember the change from Illustrator CS2 > CS3, they totally ruined the flow. It feels like they make changes just for the hell of it sometimes.