I hate that process. I resorted to buying a HDD adapter. I fire up the new machine, connect the adapter and put in the old computer's drive. Then I'm only dependent upon one OS.
Most new computers today have a data/file transfer function in the setup routine. Generally you'll need a USB cable to connect the two computers together. sometimes you can do it through wifi as well. This is the safest and generally the best method for transferring both data and files.
If on the other hand, the old computer continues to give you the blue screen of death, you're not lost—but its not a walk in the park either.
You can get a HDD caddie that fits your old hard drive and connect it to your new computer. Your new computer will see it kind of like if you put in a CD. Some will require you to mount it, while others do not.
Once your new computer can see the drive, files can be moved from the old hard drive to the new one, but again you need to know where to find things and where to put them.
Things like Outlook would require you to understand how to transfer critical files and it could be necessary to boot up the old computer and export some of the files so they can be imported to the new software. Your favorite websites and password files if you store them on your computer can also be imported.
My first computer was a heath kit. Been messing with them every since.
I'm just going to move what I can with an SD card. My old computer is a laptop, my new one is an all-in-one so I can't really mount my old hard drive in my new one. I did that before when I had desktops. Plus, I'm going to try installing Windows 10 on my old machine to see if it can be salvaged as a word processor or something. I looked for an easy transfer program, but Windows 10 did away with that and I would have to spend $15 to transfer the stuff using the software. NO. THANK. YOU!First question is does the new computer already have the data/file transfer program. Check your manual. A lot of them do.