Short summary as introduction:
We are a small Java web development team, creating applications using various frameworks and libraries like JSF, Hibernate, Seam, all together deployed in JBoss AS.
Initially, the app was put together and some features added to form a showcase to show to potential customers. Some polishing took place, the app got released, it was accepted and working and as time went by, additional features were added, bugs got fixed, new bugs occurred, as it always is.
Due to high bus factors and startup racing, development got a bit out of hand - more and more features were added, not having fully understood the core architecture of the system. It's still working, but there are always pitfalls because the system evolved from where it originated to something else and in the beginning, various shortcuts were taken to speed up development - now all this comes back and development slows down, because workarounds are used and it's fairly hard to introduce new developers into the project.
Now, I'm in the progress of cleaning up and organizing things - installing a bug tracking system, build up a testing/quality culture, thinking of how to do automated testing, code reviews (all that fancy professional stuff we were lacking in the beginning) and doing general refactoring like organizing class hierarchies and functions to make it easier to use stuff. That makes everything a bit better, but there is still a lot to do. As I'm not the person who initially build the system (former lead programmer left) and not that experienced (developing for 2.5 years now, but that's my only 'open world' experience so far), I'm not always sure what to do.
Here's my problem:
Refactoring is always something good and I'm constantly doing it to make things easier, but what puzzles me is when, how and why I should upgrade the basic architecture (that means, libraries the system relies on, application server, database etc.)
We are currently using JBoss 4.2.2 - I read somewhere of JBoss 7.1 already out, should I go for that? How can one evaluate this?
We use Seam 2.2 what seems to be a big blocker (does not work on higher JBoss versions, doesn't support JSF2). In addition, I see sources telling me to use JEE features instead of Seam.
Basically, I'm interested in any generic approach for this problems, not only the ones I mentioned in the examples above - as I may stumble over this problems for another library on another system in another time (or someone else may face similar problems).
So, what's the point? Shall I be up to date and use only cutting edge libraries or should i stay with what i have? How do I recognize, the technology I am using is literally a dead horse and jump off? How often should such technology upgrades appear?
And, another question beside the general 'how to do upgrades'-stuff. How do I recognize my piece of software could be called one 'crafted by professionals'?. Is there a Joel test for well-done software besides common programmers sense?