Can you give some examples of places that meet those criteria (good transit, walkable, major cultural venues, varied dining scene) with $200k houses?

I don’t think there are many places in America with good transit that are walkable so I think it’s going to be tough to find that for $200k. And if the solution is just to move somewhere so small you don’t need transit, then you lose out on the varied restaurants, cultural events, major airport, etc.

The better places for transit like NYC, SF, Chicago, and Denver are all major cities so you won’t find dirt cheap houses near the transit.