Q.weeping cherry
I have a weeping cherry in a pot that is eventually going to be transplanted into the ground. The question is, should I plant it in the ground over winter and dig it up later or bring it inside for winter?

If you have a the location for it outdoors now, I would plant it now and it should be established by winter (make sure to water well). If the location is not ready, then I would recommend heeling it in outdoors. This article will explain more about heeling in:
https://www.gardeningknowhow.com/garden-how-to/info/heeling-in-plants.htm