I am curious if you have tried any other USB devices
I have experienced similar issues to @Joerg.
Using tp-link TL-WN725N. Used both PC - Powered Hub - Endpoint - WiFi Dongle, and PC-Endpoint-WiFi Dongle. Connecting to a tp-link router.
I would get a good connection and when coming back after a shutdown it would not connect. After some experiments I noticed that it would occasionally connect immediately after re-flashing the SD card. After changing to a different SD card it appears to connect more reliably. The SD cards are the same brand and part number. Will keep checking over coming days to see if this has resolved the issue.
The ssh tips have been very helpful. Not a Linux guru by any means, hence the attraction of .Net and C#.
The TL-WN725N is 2.4Ghz only from what I read. Is your router maybe using the same SSID for 2.4 and 5GHz with automatic band switching turned on? Just for giggles, you might try turning off 5GHz or using different SSIDs for the two bands and join the Endpoint to the 2.4GHz SSID.
Do also use powered-hub → Endpoint → dongle.

@mcalsyn, apologies for the delayed reply. In my case it was a faulty SD card, I have had no issues since replacing the card. I am connecting to a TP-Link Router and have had success if connecting to either a 2.4GHz only SSID or to an automatic band switching SSID. I am using USB C and have monitored the current draw when using Wi-Fi and have observed a maximum of 0.29 A. Thanks.
Thank you for your sharing. We have one more option to try for other customer if WiFi failed.