Hopefully the last question in choosing an implementation language for this web app, but before pitching to anyone, we would like to know what your experiences are with maintaining an application.
We maintained (and since moved to a hosted solution) a web portal based on Perl.
The problem was that we had cases where Perl was updated or a module was updated, and since the whole website was interconnected, it easily became a nightmare because one small change in the CPAN modules could cause the whole website to die (this was an open source portal, we didn't create it) because something in the portal was very specific about what version module it would accept.
There were a couple times where an innocuous set of security updates could cause the website to come crashing apart for a noticeable period of time.
So, in deciding to create a web app based on PHP, Django, or Ruby on Rails, can people share what maintenance on the website has entailed when upgrading all or parts of the framework or language?
How "easy" it is to break or glitch the web application when just trying to install a security fix for a module/gem you didn't create? Or isn't it really an issue?