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So you have been handed a site that has Xoops 2.0.x, 2.1, 2.2 or whatever.
Before you attempt an upgrade you will want to do some research before hand.
As of this writing the latest stable version is 2.5.4 with 2.5.5 beta on the table and 2.6 in pre-alpha. There have been a lot of changes from the 2.0 series to today and they require that you do some homework before upgrading to help make the change over as seamless as possible.
You will need to do three things before you get ready to do an actual upgrade to your live site.
Make a full backup of your system's database and files before you attempt anything. If you fail to do this portion you could end up loosing the whole site and you really should be backing up your system pretty often anyhow.
Install a copy of your site on a local computer for testing purposes. This will require some changes to your mainfile.php but should be relatively painless. You should attempt all upgrades on this local copy before trying on your main server. again you want to prevent issues on your live site. It is best that you try to use a local server that is as close to the server you are using or are going to use. (Linux, MS, etc.)
Create an inventory of the modules in your system and their versions. You will want to decide which modules you want to keep and which ones you will upgrade later. The idea here is the fewer modules you have to upgrade the fewer chances for mistakes. The older the xoops you are running the more of a chance of there being issues here. This is why we backup and use a local server to test out on.. If it works to upgrade locally it will work to upgrade on your live host.
You will also need a way to access your database directly. MOST systems support something PHPMyAdmin and you should be somewhat familiar with this as you will need to use it.
Lastly, you will want to figure out what version of Xoops you want to upgrade to.
2.3.3, I believe was the first version that was built for php 5. Not sure if it is worth upgrading to this version. Since most modern hosts run php 5 now you will want to upgrade to this version at a minimum. This might make sense if you are running an old system and can't get it working with a newer xoops. This version was intended to bring the best of 2.0, 2.1 and 2.2 together.
2.4.5, My understanding was that this was essentially 2.3.3 with a major facelift mostly for admins. Because of the similarity between the core of this and 2.3.3 there really isn't a real good reason to use 2.3.3. The interface and the security upgrade are well worth the upgrade. This version is the most stable of the current xoops at this time. So if you are upgrading from an old system I STRONGLY suggest at a minimum to start with this version.
2.5.4, The latest version of xoops at the time of this writing. If you can upgrade to this version it is the best version to date but is most likely to break your old modules. 2.5.5 beta is available as well. The only modules truly certified to work with 2.5 series are in the basic module pack. Since this is an evolving version you may want to try out the modules you want to use with this and make sure it works. This should also be the most secure version of Xoops today. At this point this series is where you want to be but you may find yourself sticking with 2.4.5 if the issues are too many to warrant upgrading to the 2.5 series just yet.
Attending College working towards Bachelors in Software Engineering and Network Security.