One big technical trouble of Linux for newbie user is in Software Management. Because of the large of software development in Linux, each software package on Linux is depended on many other software packages. This condition is usually called as package dependency.
In many common cases of software upgrading issues on Linux, the package dependency is became a biggest problem and unsolvable. If we need to get upgrade on one software, we have to upgrade many other software packages or software libraries packages of our Linux system. And if we upgrade many fundamental libraries of our system, the other softwares will be removed. Arghhhhhhhhh! ^_^
The only one way to solve the dependency trouble on software upgrading is system upgrading. We have to upgrade our whole Linux system, to be able to installs the newer version of the softwares we need. Of course not all software upgrading need to be solved by system upgrading. There are many newer software in Linux that built as a universal and independent software installer (e.g. OpenOffice.org). Hmmmmmh :D
I usually imagine its will be so great thing if the software management of Linux would be simplified, as well as software management of Microsoft Windows or Mac OS X. And I know, I have to reach my imagination by my own self to realize. And for the first step, I`ve successfully re-packaged the XMMS Music Player to be a “Universal Linux Installer”. Not a big deal, but its so great!