Just curious, I'm assuming that switching to Linux to get automatic updates for all packages would cost you more than $5 in pain in other areas. Is that assumption correct?
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?
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.