I have to periodically check whether my version is out of date. When it is, I have to find the download URL, click on it, remember to come back when the package has downloaded, and run the installer. I have to do this on all of my machines.
Sure, this isn't all that much work. But $4.99 isn't that much money, either.
If paying for the software were easy for everyone who has a Mac everywhere, I would feel a little bit uncomfortable, but that would be all. My point is that this move may effectively shut off parts of the world that have no access to the Mac App Store.
Don't get me wrong: I like Apple and used Apple computers since my early days as an Apple II developer. My main computers run Linux, but I like to keep a Mac around. What worries me is that this move actually hurts Apple a lot more than we may realize at first.
It's, of course, next to impossible to develop Mac software without a Mac and, since we are talking about Xcode, access to a modern Mac is a necessary condition.
Now, if I want to update anything I type the following in the command line:
sudo apt-get udpdate sudo apt-get upgrade
... And that is all. Unless you meant some other kind of pain and suffering?