How often do people use the latest software, and right after it's release? For free software and paid shareware (which provides free upgrades) I can see this happening. As for commercial software, well let's just say that this is probably why Microsoft is offering a free upgrade for Windows 7/8.x users. (It probably partially explains why they aren't offering free updates for XP/Vista users, since these people wouldn't be buying their latest software offerings anyhow.)

As for using older open source software because that is what's packaged for a distribution, I can certainly see how that's frustrating. It is an issue when hardware support is involved, e.g. being calibre, but it is rarely an issue otherwise.