Re: But you never do.....
The problem is that I need to be sure that all the software and hardware I have can work on Linux.
The hardware site is easy. Download an ISO and burn to DVD or USB (or if you really have time on your hands set up network booting...). If you're really seriously worried about the data on your HD then shut your machine down, remove the power and/or data cables from your machine. Boot into your chosen ISO.
Now you may get something come up to say that there are "restricted drivers" available for your machine. These are often from NVIDIA, and are still easily installed - just for some reason they can't be automatically installed (I've not cared enough to look further into this, I just know message comes up, I click "install the driver" and it's done). That may need a restart (seldom), so if you've used a USB it should be able to load the new drivers, if not or on DVD don't bother.
Put in your wireless details if needed.
Open up Firefox (comes with most Mint distros I've seen - as well as full office suite and tons of other goodies you have to get separately with Windows) and visit Youtube or some other video site (or select a video you have elsewhere if you wish), and play a HD video (or best quality you have available). If you have sound and video, and of course network, then you're good to go unless you have a printer or scanner or something that doesn't work. IME most of the time they're quick and easy to find and install, but a few Lexmark and HP ones aren't. There's probably others, I don't use paper much myself so don't normally need printers or scanners.
As to the programs, that's another issue. I've found many install quite well on WINE, and there's the likes of Play On Linux and other tools to get things going that don't. I cannot recall it atm but there's other WINE-like systems out there, one maybe named "Cross Over" (can another commentard help here please?) - try them and if they work you're done with MS, enjoy a life of peace and running machines rather than stress, multi-hour multi-gig updates (with 10billion restarts) just to make a few bytes of change to a friggin web browser!), and lots of breakage.
One other thing you may like to consider.. Where I have desktops or laptops that can handle more than one HDD, I have my Windows and my Linux on separate drives - one per OS where I can. That way you're less likely to have any issues with installing and can go back to the old system easily if you really want to.