Yes, there is good chance that the USB connector of the laptop is damaged (or just dirty) and may not provide correct connections.
As described on https://www.hdsentinel.com/forum/viewtopic.php?f=32&t=12756&p=18265
the best way would be to perform a Read test on any device (which is otherwise good, working correctly) like a pendrive, SD card or external hard disk.
This would reveal if there is anything wrong in the storage chain, then the device will likely disconnect and timeout happens.
For external 2.5" USB hard disks, a very-very common problem is the insufficient power which provided by a single USB connection. As a result, the hard disk may not work properly (very frequent cause of weak sectors and even failing drives).
Not sure, but if you have the opportunity, maybe try an USB hub with external power supply (which will not drain power from the laptop) as it can greatly improve the stability.
> Clean the USB ports (Suggestions? Use IPA on a Q-tip?)
Personally I use WD40 for cleaning connections, not sure but others may work too.
> Windows 10 re-installation that keeps all programs and data.
> Try the above Microsoft tool.
To be honest, I do not think these would help in any ways....
Maybe you can check if there is a BIOS update available and if that may be related to the USB controller of the laptop but I do not think so.