Distribution

Your decision will depend on a few things, IMHO:

• what your ultimate goal is with respect to the use of the system;
• the level of support a distro receives from it's publisher and user base; and
• your level of experience with Linux/open-source in general.

Some distros are designed to be easy to use with lots of fancy GUI stuff that is mostly worthless in a VPS environment (e.g. Ubuntu or Mint). Others are for ardent system hackers who want absolute system control (e.g. Arch or Gentoo). Most lie somewhere in between…

Since Linux distros are free, the only penalty you pay for switching to a new distro is the time/effort it takes. Most of the distros that are hyper-easy to set up and offer lots of goodies are the hardest to move away from. This is by design. The hacker-oriented ones require a great deal of time/effort to leave behind because you've had to customize them so much in order to accomplish your purpose.

For the vast majority of distros between these two extremes, migration from one distro to another is a fairly easy process…not free but mostly painless with a little advance planning.

-- sw

I had a lot of similar things that @stevewi had above regarding choosing a distribution, though they beat me to it.

That said, I also wanted to cover some Linode specific aspects of this. To help you get started, I wanted to provide links to some of our guides geared towards people new to our platform and new to Linux:

Getting Started with Linode: This is a great primer to get a Linode server up and running. It covers the important steps.
Linode Beginner's Guide: If you've used shared hosting or other providers, there's a chance their product offering could be different from what ours is: infrastructure as a service. This guide is a good outline of what makes us different than some of the other hosting providers.

We also have a bunch of other "getting started" guides that cover a lot of other aspects of working with Linode, Linux, or cloud hosting in general.