As far as I know, Windows does not measure the time itself. There is no reason to do so.
If there is any solution to measure the time, C++ would be the best choice. Because you need to add some kind of low-level handler that is triggered by the plugin event. When an USB device is plugged in, a
WM_DEVICECHANGE / DBT_DEVICEARRIVAL
message is posted to all top level windows when the device is ready for use. This can be used to detect the end time. But detection of start time requires hooking deep into the kernels USB driver.
This link describes what happens upon plugin [^