You can always ask, this is the idea here.
However, this is a Forum of (mostly) commercial software and we cannot discuss how to by-pass trial version restrictions of some other commercial software. With commercial software, the basic idea is that you pay for them.
Since you are talking about old software, there is a very likely chance that you find Open Source software, which is much better than your old commercial software. If Windows doesn't provide it, try some Linux, like Kubuntu or Ubuntu. By default, you get and see much more software than with Windows. For instance, Ubuntu Studio has basically tens of different tools for all creative aspects (photography, video, music, players, writing, graphics) and many others can be downloaded. There are many more dedicated distros.
Now that you already use VMware, there is no practical limit how many different systems you can try out.
