Imagine trying to find a blog post explaining why your 4 year old version of an image upload gem doesn't work on JRuby. It's no fun :)
This really depends if you are running a hobby on a server, or running a business. I update client side apps cause it is exciting and it doesn't matter to me if it breaks. If it does, we cry foul and the developer updates a patch hopefully within a few days or weeks.
On a production environment, this is much different. There's a reason why people say "if it ain't broke, don't try to fix it." A down time of 5 minutes could cost one company thousands while another company millions. If the cash printing machine is down, having a broken image uploader would be the least of their concerns.
Yes, you have the code for Rails and can fix/make changes, but the further you deviate from what other people are fixing bugs in, the less you benefit from using open source.
If there's a bug or security hole in Rails 2.3, we go in and fix it for our users and ship it immediately.
Forking off your own special version of something is a recipe for eventual pain when keeping up the old version is worse than upgrading.