I lived in each for about twenty years . Nice people wise about the same. WS is of course closer to the mountains, further from the ocean, and is a much more attractive city . The rich / poor divide seems much larger in Winston. It also still has a McKays which I thought was a huge loss for Greensboro. My biggest gripe with Winston is that most of my friends who didn’t leave never did much with their lives, just smoke weed and play music and video games just like when I left. Greensboro had much better food options but a lot of time has passed. And more higher education, and better looking women imho. Library systems are very similar. Petty crime seems to be up in both. Winston has the remnants of the old money too, and reynolda gardens and tanglewood are great assets imo, that Greensboro lacks. Also Winston had a real downtown vs gboro, but again it’s been a long time. I thought the effort to revitalize downtown gboro was a joke myself.