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I'm rather new to linux; Basically I've just used it now and then when I've had to set up or manage web applications; so the only exposure I had was when I SSH'ed to a box. Now I've started using a Mac running OS X 10.6, which I guess is based on linux / unix.

Anyhow, I'm now looking into setting up my own linux laptop and linux server; and my predicament is this:

I feel like I can use most of the shell commands I need to get around, move files, and edit config options, but I really can't tell a difference in the flavors of *nix!

At what point do you see a difference? And without knowing the differences now, and how do I choose one to start with?

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I would say that you would want to think about how much Linux you wanna learn and what for. For desktop enviroments I would recommend Ubuntu since its easy to use and theres (almost too) many ppl running it already and hance you'll have help fast if you stumble on a problem.

However, if you really want to learn Linux I would recommend another distro, namely Gentoo or another that you buold from scratch such as LFS (Linux from scratch). Those distros take alot more time to install and maintain but will help you understand alot more in the long run.

However, trying your way forward is the most important, if you dont like a distro then just try a new one. Also, Fedora/Centos is even bigger then Ubuntu, so if you dont like Ubuntu, try Fedora/Centos out.

Good luck!

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Linux distributions recommendations for servers

That has a lot of information about picking a distro. But the key differences between distributions are in:

  • Package management (.deb vs .rpm vs. others)
  • Administration GUI differences
  • Layout differences in /etc
  • Default choices for packages

Pick one you like and stick with it. CentOS is real big in the VPS and shared-hosting space, if that's a concern for you.

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For a complete newbie, I recommend "Whichever one your friends use", as that's the one which will get you the most support. If your friends argue, then only you know which ones are full of @$%# and which ones have clue.

If none of your friends use Linux/Unix, then aside from questions of "how do I make new friends?" :-D there are two approaches:

  1. Attend a Linux User's Group meeting. There are LUGs all over the world. They tend to meet once a month and will have people happy to assist a newcomer in getting set up. Some have "installfests", meetings dedicated to helping newcomers get set up.

  2. Failing that, figure out what you want to do and why you want to play around with Linux

    • If you just want to try it out as a desktop OS, use something user-friendly and approachable, then "Ubuntu", from Canonical. They have put a lot of work into the "final 10% that takes 90% of the work" to really make things shine.
    • If you want to get experience with something that will help with employability, then perhaps CentOS, because it's effectively RHEL without the support.
    • If you want to really learn how things work, because you're eager to see how things fit together and you're the sort of person to strip a car engine, then as xeet says, LFS, Gentoo, or I'll add Slackware to his list.
    • If you want to learn OSes and see how things work, have a coherent system and don't mind less hardware support, FreeBSD, which isn't Linux. Note that unless you have some local support (LUG, friends), going the BSD route will isolate you more. Very nice systems, though.
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Following up to sysadmin1138's answer, it might be worth going for a distribution such as Redhat, as there are training/certification available for this. This would prove to a new employer that you had these skills. If this is a concern for you.

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There's a couple of big ways in which Linux distributions differentiate themselves.

Package management

A package manager is a centralised system that keeps track of all installed applications and the programming libraries they depend upon.
The most popular ones are based on rpm packages, found in Red Hat, Fedora, Mandriva, Suse,... and deb packages, found in Debian, Ubuntu, Mint.

The desktop environment

Not relevant for server environments, but definatly a key differentiator in desktops. The most well-known desktop environments are GNOME and KDE, the somewhat lesser-known ones include XFCE and LXDE. Most distributions offer one as the default, but also give you the option to change to another desktop environment. So don't be afraid to try them all out.

Other differences

Some other differences between distributions include what system they use to start processes at system boot (sys V scripts, rc.local file, ...).

Personally, I'd recommend using Ubuntu for both the desktop and the server. They have by far the largest community on the web (including a sister site to serverfault called ask ubuntu), and is generally regarded as a great distribution for beginners such as yourself.

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