Obviously New York , but do most major cities have enough tall buildings to let a Friendly Neighborhood hero get around?
Every city that has any tall buildings has enough for the web-swinger to get around the part with the tall buildings. And every such city has a far larger low-rise or no-rise outer urban, then suburban, periphery where web-swingers are walking, not swinging.
Your question is a tautology.
I was also disappointed in this thread (heh!) contents.
I thought it’d be about which cities were good for people to use Tinder, et al, to meet strangers for one-nighters. That sort of web-swinging is the game everyone can play, not just superheroes with silly taste in clothing. Although NYC might be a good choice for that kind of swinging too. 
This post begs for this (Spiderman in Kansas):
To the OP he could certainly get around downtown Chicago. Probably most major cities (City of London, Hong Kong, Singapore, downtown Tokyo to name a few.
Is that really called web-swinging? Huh.
I just assumed that New York was more smooshed together than other cities due to lack of space, thus making it better for Spidey.
I have no idea; that’s not my bag. But it sounded like a logical name and before I opened the thread I thought you were informing us and soon we’d all learn from each other about internet app-mediated hookup culture. I guess not.
If I didn’t think I’d get sued into oblivion by Marvel I’d trademark the name right now!
Apparently, he has trouble hailing a cab in NY.
On a related tangent, how would web swinging in a city work, exactly? You couldn’t really attach to the side of a building, could you? It seems like gravity and physics would dictate that you’d just smack into the side of the building.
Seems like you’d always have to hook your web to something horizontal with nothing underneath- like the ubiquitous flagpoles in old movies or cartoons that characters would grab onto when they fell out of a tall building.
ETA: I actually put some brainwork into this, and I think I got it— if the buildings are close enough together, you shoot your web at a building ahead and on the other side of the street or whatever. You swing forward and toward that building, and before you smack into it you shoot a web at a building ahead and on the other side. So you advance in a bit of a forward zig-zag. Mistime it though, and you get smushed like a bug 
That’s what i expected, too.
Not that i know of, i figured it was just a cute way to describe it, though.
I’m going to take that as a compliment even though it wasn’t at all what I meant!
There’s still some zigzagging, but it’s not as bad as that. Each swing doesn’t need to be planar. Think of Spiderman as playing a game of tetherball: Even though the pole is vertical, the ball doesn’t usually slam into it; it swings around it. So you web to a building ahead and to your right, and swing around until you’re past it, and then switch to one ahead and to your left, and swing around past that one, and so on.
That was the best thing I’ve seen for days! Now I’m imaging a rural Spiderman who makes parachute webs and catches the wind, like the actual spiders do.
There aren’t many cities where you could reasonably swing from skyscraper to skyscraper and get very far, especially in the West.
I think you need to contact Greek spiderman to teach him the correct technique.
Spidey has incredible strength. He can kick off a building at high speed, or run along the side or top of a building at high speed to pick up momentum. He can also lengthen his web at any time. He has much more ability than Tarzan who was limited to existing vines even when in the jungle. When he was in New York City the lack of local vines left Tarzan with no choice but to run along window ledges and eventually jump off one of the Brooklyn Bridge towers into the East River.
I would assume in any city or suburb where there are NOT enough high-rises or skyscrapers Siider-Man would be jumping from roof to roof with someone more akin to parkour.
I just hope he has some good parkour luck to get around safely.
And, apparently, buffalo, too (well, most of them).
Kin to Peter Parkour?
You! Go to your room! Bad @gnoitall, bad, BAD!
Seriously that is really clever. Got a big grin outta that one.
It’s amazing how often you and I have parallel thoughts when some topic or comment can be mis-construed salaciously. I wonder if our spouses would object to an IRL meeting? And which city would be best? 
I’d like to know how the gossamer thin web strand manages to hit whatever he’s aiming at, what with all the swirling air currents.