You might want to check out "Nexus Root Toolkit". It's a Windows program that wraps up various solutions. For example, it will walk you through installing the proper drivers, adb, fastboot just so. Also, it can restore stock roms which is nice if you're getting worried about owning a brick. It is a little out-of-date (still wants an older version of TWRP for one of its steps, not a big deal), but I found it worked well for my Nexus 7 2013.
Note that the UT installer didn't recognize my device either. I always had to select it by hand.
I also installed Ubuntu 18 in a VM using VirtualBox. Then, also Ubuntu 16 the same way. What ultimately worked for me was ubuntu-device-flash (only available in 16 afaik, it's the old way I think), though my case was strange and I'm not recommending that for you.
It was definitely a bit tricky to get my usb ports working in the VM. I had to go into the vm setting and add them (and they changed a few times as I re-installed windows drivers). My impression is that you still need to get the usb drives for windows right as the VM piggybacks on those. Even so, I was still unplugging and re-plugging the device at times to get the usb connection to wake up.
The manual install is doable, probably a little easier on Ubuntu as it needs wget and a couple other things that are not native to Windows (but I was able to install them without much trouble). Doing it manual can help you zero-in on the problem as I found certain steps would fail. The UT installer doesn't seem to check for errors much, so it's hard to tell where it went wrong (imho). You can also use "adb shell" while in recovery to poke around on your device to see how things look (it's like a pathetic little linux install in there). If you're comfortable with that, not essential.
I had 3 cables, one of which was definitely bad. "adb devices" did not work at all for that cable. So, I doubt your cable is bad as it seems to work mostly.
I think your best bet would be to use Nexus Root Toolkit to do it's "Full driver installation guide..." (button near top). It has like 4 steps as it makes sure every little piece is right. I suspect I had initially some issue with not being in MTP mode or having some old windows drivers still installed (it made me delete devices, etc.)
Anyway, good luck!