These things can be fixed by automatic check for updates and preferably seamless automatic update, but the problem is that people who normally like open source don't like automatic updates. People don't like when they're asked too much questions ("Do you want to check for updates?" - Yes - "Do you want to download update?" - Yes - "Do you want to update now" - ffs just do it!) and they don't like if program does this kind of stuff silently in background. How to fix this problem?
people who normally like open source don't like automatic updates
Really? Where does that come from? Because one of the things I love most about running Ubuntu is that everything just stays up to date on its own. I'm always very wary of installing something myself and will nearly always take the apt-get route unless I really need that very latest feature.
Whenever I evangelize running linux, (which is very rarely) this is one of my big selling points. When people see the update manager pop up, update a bunch of programs while I'm doing other stuff and not even ask me to reboot they're often convinced to give it a try.
There's one other benefit of Ubuntu that is worth pointing out: there's only one source of automatic updates. The auto updates on OSX and windows drive me nuts because every app has their own updater with their own UI and their own preference for whether and when and how to update.
You fix it by giving Windows and OS X package management. It's not something one app provider can do (well, maybe Apple could bundle it with iTunes...)
