My server selection has always been on auto. The only time I’ve ever gone to a manual selection was when joining a couple of community events. Then it goes back to auto when I’m done, typically connecting me to USA East.
Live Weather worked fine for me (except at launch, which they fixed in a patch in September) until the last November update. That’s when it stopped working. Literally, I was flying. Update dropped, so I restarted to get the update. Weather worked the first flight after that and then not on subsequent flights with out a restart. It hasn’t worked since.