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And I've not played TF2, but Unreal Tournament 2004 works great on Slackware.
What security threats? If it works, dont update. Just like Firefox. Never update unless you NEED to do so. Every update will 99% BREAK one or more THINGS YOU LIKE. If you are running a company server yes, maybe updating is needed. If you have a router with NAT, firewalled, you have no security risks anyway.
Yes, you should really upgrade.
And not only for security reasons...
Also using another distribution can be a good idea (i hate ubuntu), but it just makes no sense if you are using Ubuntu from 2009 and you like it. just upgrade.
And... Actually Wine shuld works pretty well on the last ubuntu version, probably better than on the old version. why do you say it's worst?
Well... probably you need some missing library/driver. Ubuntu has a lot of them pre-installed.
As a server admin, I should slap you. Corporate systems are the least likely to be upgraded, even to LTS releases, its advised, but most companies will refuse to do so, just take a look at all those WinXPs still all over the place. In companies there are often specially designed programs that may break on a new version. I don't think you understand what kind of security threat I am talking about. There are always loopholes around a lot of things, security threats can include exploits that can bypass you, who cares if you are firewalled and behind NAT, you are still open to attack from anywhere. Be it from your own internal network, to the external, even a simple virus. But there is more to it than security threats, you lose support of software applications, this means no more upgrades for your software unless you manually download source code and install it, no compatibility with hardware released after that time, so if you suddenly buy a new printer it will not work, and flatout performance improves in both the new, more stable OS, new features that will increase producitivity, and a wider assortment of free software in the software center. Not to mention, wine is a great example. If you have the latest Ubuntu, you can easily install the latest wine, not so much for older versions. You should always upgrade to the latest version, it only takes a few buttons or a terminal commands to upgrade, you have a lot to gain and nothing to lose. By the time your system cannot handle newer versions, it's well time to upgrade.
But you are right.... it's always better to upgrade, specially on Linux.
New kernel, lighter system (well... maybe not if you are using ubuntu .-.), all is much stable.