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This is a bit tricky, but it is tricky more because of XO/OLPC than linux. I hadn't looked very hard at the underpinnings of that before but from what I see ( )

it looks as if applications ( especially appliactions with a graphic interface ) need to be respun to be usable on XO/OLPC. So my hunch is that if you don't see the tool that you need in the interface, and there isn't an obvious update/install utility where you can find load such a tool, then you might be out of luck. But, again, my XO/OLPC knowledge is limited to some quick searching.

I can unpack some of your other questions if you'd like ( not sure it will help but.... )

Non-esoteric linuxes have become pretty friendly to update and use. This is largely because groups of people ( some commercial and some not ) have taken on the job of handling interdependencies, grouping compatible versions of software together in distributions, and keeping distributions patched until deprecation. Debian, Ubuntu, Fedora and Suse are some of most influential such groups of people. Redhat, which you mentioned is one as well. After their release 9.0, they spawned Fedora to provide desktop and leading edge software, while focusing RedHat more on enterprise software.

These different groups generally ( but not universally ) manage software versioning, integrity, and interdependency through packaging systems. These basically work by wrapping the software to be installed along with metadata about the software, scripts to be run on installation, and things like that. There are several different packaging systems. The two most prevalent are rpm and deb. Redhat based distributions use rpms. It doesn't matter much to the end user unless you are web searching for software to add. On an rpm based system you typically need to find (a) the software that you desire (b) packaged using the packaging type for your system (c) built to play nicely with your distribution at its current release level. Typically you don't even need to do that. On recent Fedora distributions, for example, you can just use a command line tool ( or graphical tool ) to ask for software by name, and it will go fetch it for you along with any dependencies that it requires, verify it all, and install it. You don't need to know anything about rpms or debs, which version of a distribution you are on, or even which distribution you are using. The other weekend my girl needed to view a Powerpoint(tm) file on her laptop and couldn't view it. I told her to type yum -y install and she was good to go.

So the linux part can be easy with fairly recent distributions. Different folks like different distributions but most of the major desktop distros are very friendly to use and update. I know many people who find Ubuntu to be very easy to use and I've had good luck with Fedora.

The trick is that XO/OLPC is very much a niche beast. There may well be an app that will do what you need on XO/OLPC. I'll try to dig when I have some free time.

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