Wow. Not only are you using Windows (cringe), but you're talking about ancient versions of all the software involved.
I would say find a separate box you can play with, and install the latest (stable) versions of all software - PHP5, Apache2, MySQL (4.1 at least... 5 if you want). Once you do this, configure it up so that it's similar to your current setup. Then... TEST. Turn on verbose error logging for all software and run through as many of your applications as possible. If you can do it on similar hardware, you could even do some stress/load testing as well.