I was thinking about what makes images like this so charming, vs. looking out at most cities.

I think one reason is that it is a composition of a lot of small human-scaled cozy places.

Our cities could learn a lesson. Classical architects must have understood this.

There is something comforting about seeing human scale elements - balconies, 3 storey buildings and towers, embedded into a much larger building.

You could be placed anywhere on this building and not feel out of place.

If your town must hire someone to draw up a master plan, hire a theme park architect.

They have real world experience building lovable places.

Here's a list to get you started:
themeparx.com/theme-park-des… Regarding the cheap-feeling of theme parks. This has to do with fake materials (styrofoam, fiberglass, stucco, etc. painted to look real.)

Counterexample:

1) Cheap strip mall architecture from a real town.

2) A theme park with real materials.

The latter feels more authentic.

I'm told we build glass and steel towers because that's what companies want.

Yet the most profitable tech companies are prefering traditional buildings for their NYC offices.

Photos are the NYC offices of: eBay, Google, Facebook (currently), Facebook (future expansion) Netflix, Twitter, Slack, Apple/Adobe.