Normally, I choose autopsy from the start menu to get going when I am trying to recover files. The procedure may seem a little klunky, because it is meant to be suitable for true forensic investigation. You can skip some of the stuff required for forensic case studies.
The documentation for the latest version is much improved.
CAINE provides a Linux-based boot environment that can recover even deleted files, and recover parts of partially overwritten files. One big reservation: I've only once tried it on a Win 10 HD and that did not work out -- it was not my HD and I did not set the security/privileges etc. so that may have been the problem. I have not tried the latest release of CAINE on Win10. BUT ... there is also a set of tools specifically for Windows, which I haven't really tried out.
Visit https://www.caine-live.net/ and see if it's for you. It's recovered many files for me, even ones deleted by sysadmins.
ETA: CAINE can be loaded on a flash drive, and the d/l should take less time than Win10. 
I'd give the roommate's iMac another shot -- remember most browsers let you restart a d/l from the file saved so far.
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