MSFS2020 asks me for generic settings each time I start the sim

I’ve had this happen occassionally, but so rarely that I haven’t bothered to try to figure it out. My first guess that information is stored locally somewhere and it either isn’t getting found or isn’t able to be loaded. If nobody has an answer for you, I’d start by downloading ProcMon (which is an official Microsoft tool and can be run from the download without any installation) and monitor flightsimulator.exe while it starts up. You’ll be able to see all of the file activity and hopefully something will jump out that might give some insight into what is going on. You’ll also be able to look at registry activity; perhaps it is looking for your information in the wrong place…