Flat cities with a rigid grid are kinda boring and often downright depressing (standing on a street in some of Chicago's neighborhoods, with ticky-tacky little houses marching uninterrupted into the distance as far as you can see, is a soul-sucking experience)...

Limited horizons and change make things interesting. You don't want complete chaos, because things also have to "make sense" to some degree (so complete randomness, like a stereotypical suburban cul-de-sac maze, tends to be bad), but variation is a good thing.

[A nice city to look at for interesting approaches to urban structure which are both somewhat regular, but more interesting that a grid, is Edinburgh, which has seen successive waves of fairly successful urban renewal over centuries, resulting in one of the most beautiful and fascinating cities in Europe. In the "new" parts (150-250 years old as opposed to the older and more organic medieval parts), Edinburgh streets have such features as small localized grids, sized as to with care to avoid large-scale monotony, occasional "circuses" acting as focal points, streets in gentle arcs which are practical for transportation, and yet maintain a constantly evolving street view and horizon, terraces along the sides of parks, etc.]

In defense of Chicago, its grid is amazing for being able to efficiently travel around the city. The street numbering makes it trivial for any local to find their way to an address like "X00 W Belmont" without a map, and obviously the lack of hills makes for easier biking and public transit. It skews more towards beautiful architecture than beautiful landscapes, and has its share of decrepit neighborhoods (as does SF), but I don't think many people would describe it as a "soul-sucking" place. Different strokes.

I didn't say Chicago was a soul-sucking place, but rather that certain areas in it are (apologies if that wasn't clear), and one of the main reasons they're that way is the incredible sense of monotony due in large part to the regularity of the grid (there are other reasons for monotony in those areas too, of course, e.g. the rather extreme lack of variation in housing stock, the complete lack of anything except houses, and the very flat geography).

It's a localized example of the effect urban structure can have, not a denigration of the entire city. So, please, don't take it as a dig against Chicago; I rather like Chicago in many ways, and much of my family lives there. I used the above example only because it's one of the more extreme cases I've encountered.

As for the "it's easy to find addresses!" argument in favor of large-scale grids, well, yes, but in my experience this is fairly unimportant for the actual residents of a city. Most people don't spend any significant amount of time travelling to completely random locations, and to the extent they do, every city evolves methods of way-finding that suit it. I think it's much more important for the residents that the city actually be a nice place to live, and part of that is being beautiful / interesting.

[For tourists, yeah, extremely simple way-finding can be a significant advantage, but I don't think cities should be designed for tourists over the needs of those who live there...]

It's a bit of a straw man there. The NYC street grid system was meant "to unite regularity and order with the public convenience and benefit and in particular to promote the health of the City ... [by allowing] a free and abundant circulation of air". ("Foul air" was thought to cause disease.)

Salt Lake City grid system was also not designed for tourists. It was designed for travelers, yes, and I believe it was part of the vision that SLC would be looked at as a model city, with a strong Cartesian/classical influence. According to Wikipedia, "In these western cities the streets were numbered even more carefully than in the east to suggest future prosperity and metropolitan status."

Also, a grid system made it easier to subdivide the land which was newly part of the US.

So to say that the grid system is influenced by tourists is a bit of an exaggeration.

Another important part of the New Town of Edinburgh (i.e. the 150-250 year old bit) are shared gardens, which are effectively private parks where locals pay a small amount per year. For example, here is the website for the gardens we use:

http://www.belgravecrescentgardens.co.uk/

I agree that these are nice, but ... I lived in a number of flats in Edinburgh with nice (shared) gardens, but I don't think I ever used them even once. There are soooo many other cool and pretty places within easy walking distance...

[I lived there in the '90s, though, and I'm a bit scared to return for fear that the city has been ruined by its new-found position as a seat of "power" (haha); the sharp-suits crowd, "gotta pave over that park and widen those roads for my flash car!", etc...]

http://www.npr.org/blogs/krulwich/2012/09/12/160996525/odd-t... is a good read on the topic. very interesting visualisation idea that actually makes some intuitive sense.

Never said I wanted SF to be flat :] just that the comparison is not as black and white as there are circumstances to consider.

I definitely would not trade hilly SF for a flat SF.