>Streets doesn’t have their own “personality” and you have to learn them by name.

I've lived in both types of cities, and actually even the most grid cities like Salt Lake City, have parts that are named as opposed to just numbered.

I prefer the numbered cities for finding way around.

Finally I don't think the everything appears the same is integral to it being a grid city, that is instead a side effect of American habits of rebuilding often so you end up with everything relatively new and in the same styles. That is to say the stylistic affect is orthogonal to the grid, although they are both found to coexist this is just a historical coincidence.

>I don’t know half of the street names of the city I grew in, but I know where I am by the way they intersect and twist around in interesting shapes…

I don't know where your city is, but I did notice many years before everyone had a phone I was in a class in Copenhagen and everyone in the class had lived in Copenhagen their whole life and then someone talked about an address and nobody knew where it was so someone had to go out to their car and get a book of maps.

Of course Copenhagen was also built to be potentially confusing to invaders, as I understand it, and I have often thought I was walking towards a particular destination to find I have either been walking away from it or perpendicular to it.

I also find that I prefer websites that are easy to navigate than ones that have character but are confusing. But I do prefer art that is apt to be confusing and intellectually stimulating to things that are simple and clear cut.

I think perhaps the problem is I just don't want going shopping in an unfamiliar part of town to feel like a surrealistic event.