Do I Have To?
Do you have to upgrade your hardware? If everything is working and you haven't changed any of the software you were using when the machines were new, the answer is probably "no." Chances are, though, that one or more of the software companies you work with has upgraded its code, and each upgrade typically requires more computing horsepower. If you've added or want to add features and capability, you'll probably need to upgrade to make them work better than sluggishly, or at all.
If you're still using Windows XP (or something older), you should know that support for XP ended in July. XP will still work, but Microsoft is not producing updates and service packs for that operating system, and that leaves it open to attacks from viruses and other threats. Vista, the operating system that followed XP, was reviled by many, but has now been supplanted with Windows 7. Win 7 is a very stable and reliable product, but your hardware may not run it, and the software you're using may not run well under Win 7. To see if your computer will run Windows 7, do a search for "Windows 7 Upgrade Advisor," then download and run the program. To see if your software will run under Windows 7, you'll probably have to run your software under Windows 7. Fortunately, you can download a 90-day trial version of Win 7 from the same place you get the upgrade advisor.
It's also possible that your hardware is just wearing out. Computers used in the field - especially in cars - are subjected to extremes of heat and cold, direct sunlight, constant vibration, spills, dust, and moisture. They get dropped now and again. In short, they wear out. When they do, is it possible to repair or replace individual components, or is an entire new setup called for?
Much of this decision depends on what make and model of computer you have, what is broken, and/or what you need the computer to do that it isn't able to do now. Sometimes you can do a transplant, and in other situations the best thing is to let it go and give it a decent burial.