Last month, I bought the most recent version of one of Adobe's Creative Suite packages, the first time since 2006 or so. My version of Photoshop in particular was getting pretty old, not to mention Premier, which was the thing I most wanted to update. Adobe was doing a half-off the full, non-upgrade version for people annoyed with Apple's re-do of Final Cut Pro, so I figured this was the best deal I'd get any time soon.
But what's annoying about it is the realization that when software gets upgraded or replaced, the old version has zero value. That's annoying. I don't remember what the old version of CS cost five years ago, but I'm sure it was more than a grand, and now it's worthless. It was worse when giant manuals came with stuff. I tossed the fifty pounds of books that came with the old CS, and I remember doing the same with Final Cut Studio a couple of years ago. My now fairly ancient version of Avid is still following me around too, which makes no sense because I'll never use it again. It had a hardware USB dongle, so maybe that's why it feels more important. I need to throw it away.
To Adobe's credit, they introduced a subscription model, which is fairly cost effective if you need or want the latest version all of the time. If I'm content to go five years between upgrades, it probably matters less for me.
It has been different with Visual Studio, because I've never had to buy a retail copy, it's just the core of my MSDN subscriptions over the years. That's the way it should be, for expensive software.