Linux… the big question

I consider myself to be fairly knowledgeable about computers… I can
only imagine how people feel about Linux, who know less than I
do.  I want to use Linux, but this is why I currently do
not…  Mainly, it confuses me and I’m uneducated about it…

    * There are so many distros that I’m not really sure
which one fits me.  I don’t know which one would fit the uses I
plan for Linux.
    * There are two main GUI wrappers (KDE and
Gnome).  I don’t know the differences and it seems like I have to
target one or the other for any GUI apps that I develop.
    * I like that I can go to Windows update and get all of my updates at once, in one [sort of] clean process.
    * Installing software on a linux box is a
pain.  (this comes from my previous toying with linux a couple
years ago).
    * Recompiling the kernel… yeah, I tried this one a
couple years ago and it didn’t work out so well for me.  As a
daily user, I shouldn’t have to recompile the kernel.  If I were
writing device drivers, it may be different.
    * File sharing… maybe this has changed, but I
remember that sharing files between windows and linux (using SAMBA) was
not trivial.  This is a must have…

So what am I looking for specifically?  I want:

    * A flavor of Linux for development.  My
current setup is Windows XP/2003 with Visual Studio .Net 2003.  I
currently develop web apps, primarily with the occasional gui/console
tool.  It is generally written with  I have to
admit that I like what Mono is doing, but I’m not sure what web server
easily works with apps.
    * A flavor of Linux for a webserver.  I host my
own website(s) and wouldn’t mind using Linux if it was a transparent
    * A flavor of Linux for casual web browsing, mp3
playing, and office apps.  I often have to setup/reformat older
boxes for people.  If I could install linux for them, I would…
this is tough, since those people know even less about computers than I
    * Automatic updates.  I’m not a fulltime
security geek… I want my applications/OS to tell me when updates are
needed…better yet, the apps/OS could auto download and install
updates on a schedule.  I have no problem downloading updates and
clicking a button to install them.  I just don’t see myself
keeping up with patches/updates without this feature.  This should
include kernel updates with a once click (or similar) method to update
to the new version.

That’s all for now.  So if anyone reading this knows a lot about
linux, or if someone you know would, I’d like a couple of these
questions answered.  You could convert a fulltime windows user to
a part time windows user, if things were more clear.  A feature
comparison chart for distros would be nice.  Also, feel free to
debunk any myths that I might have raised in these bullet points.