I think your approach is not appropriate. First, you must check compatibility of your computer. First video card, most of the problems that arise in a Linux, are related to this particular aspect.
Then you must check the other devices that come with your PC, WiFi card, printer, scanner and other similar.
Google is a good ally in your initial search. Once you've narrowed the search, download linux distributions that best fit your hardware. The vast majority of them have a live test medium (livecd or memory stick) and tests before proceeding with the installation.
Yes, liveCD is good for testing the hardware compatibility, but otherwise you try to make this uselessly complicated.
The hardware support determines if you can use Linux at all.
If there is a device driver for a certain gadget, it is typically included in every mainstream distro.
If there is no such device driver then you are in trouble. You will not find it from any distro however much you google.
There are exceptions of course, like a binary driver from a manufacturer which is compiled for one (old) Linux kernel version only, but if you must depend on binary drivers then you are in trouble anyway.
It means you should try one of the main distros first. If something does not work then make more plans.
The only real exception for this rule are old computers and other hardware. "Old" in this case means like 12 years.
Then you need some hacking spirit anyway and my previous advice does not apply.
Finally, I recommend a distribution that offers support for as long as possible. Linux is not Windows, so you should not expect a version that offers 10 years support in the way that Windows XP does. Most distributions release a new version every six months, and the support for them lasts only 18 months. A LTS Ubuntu or Debian fulfill this aspect. Red Hat offers 10 years of support, but you have to pay for it and it is not a distribution for desktop.
Again I disagree, sorry.
Now we are talking about personal development machines. Who cares about 10 years of support for one distro version when you can anytime download and update the latest version. At least I would not want to use a 10 years old version in any situation, they are advancing so rapidly.
Besides, support from different Linux forums is free.
As for the possibility of an installation in a virtual machine, and because surely you will use to perform the programming, I only recommend it if you have your computer resources to emulate powerful hardware, with at least 2 GB of RAM.
The virtual machine does not affect raw CPU speed much but it affects the file cache speed a lot because all file operations end up to Windows.
Fortunately taazz wanted a dual boot instead of virtual machine.
If really Red Hat 3 was the last distro he saw then a modern distro with a desktop system will be a mind-blowing experience.
Juha