Software / hardware harmony is a tricky business. It really boils down to two strategies.
The first is what I call the lockdown model - which is what you've largely done and is often the model followed by people who MUST have a reliable system to do their work. This involves freezing the system at a known state where the hardware, OS and relevant software all work reliably and you can accomplish your tasks with a minimum of hassle. The upside is you come in, do your job, go home and don't have to think too much about the tool(s). The downside is if something breaks (usually hardware) or you need to change to a new software and it has been a long time (in computer terms) since there was any change, you often need to upgrade/update a LOT of stuff all at once - which is expensive, painful and highly disruptive.
The other model is the "merry go round" model. This is where you are on a gradual upgrade/update path. You wait a few months after new versions of your software come out which gives the early adopters time to identify and sort the issues. At that point you can often update/upgrade with a level of certainty the system will work. The upside of this path is you stay reasonably current with hardware, OS and software and, since you've done this gradually but continuously, the costs are spread out over a longer period of time. The downside is there will be hiccups and the system will need more troubleshootiing if something unforseen in the necessary installation goes bad.
In either path, it is imperative to keep a good working clone of a "known to be good" version of the system (OS & software).
Ian points out a good strategy to start the migration to a new OS. A partition with the new system/software to test that can be booted from your existing system is a time honored protocol.
One thing is certain, the great river of technology is not slowing down and if you make your living swimming in it, you must pay attention to where it's heading. This means trying to stay aware of the trends and thiinking over the horizon about how all that is going to affect your work.
Good luck,
x