Nothing I don't usually face anywhere else, which is to say that it's mostly the people. Cities aren't that tough to navigate once you figure out how they're laid out or you get a guide or travel with a friend. Entering a building with no braille labels is annoying but it's pretty easy to find a sighted person or two for help. I find navigating in rural and farm areas considerably more difficult because there's not much traffic or other sound cues and you will almost certainly trip on that quaint dirt road.

Uneven/unmaintained sidewalks.

Random street furniture in front of businesses.

Subway stations that are not laid out consistently.

Addresses that do not indicate that the business is actually in a small alley or behind the main building.

Homeless sleeping or sitting in transit station walkways. Frequently they sit along walls, but that is exactly what cane users use to keep square/orientated.

Frequently there is no way to tell if an intersection contains a crosswalk.

Transit stations utilized by a large number of buses.

Metro operators who don't know the system well such that you can't ask them where the connecting bus stops to pick up passengers.

Blended curbs (wheel chair ramps) are universal design, but they can be difficult for someone to detect who is new to cane travel. Truncated domes are a huge help, but they aren't always as easy you detect as you would think. They also don't always make sense regarding where they are placed.

seconding that it’s mostly the people. in rural settings, lack of public transportation or walkable cityspace is a big thing—but in cities, it’s

1. unsolicited help and harassment. i can’t go anywhere in our city without being solicited, and i definitely can’t be alone without it escalating.
2. the amount of people makes it hard to travel. crowded areas are a special kind of hell where people don’t see your cane, try to jump over it, etc.
3. also, people driving like idiots (though maybe this is applicable everywhere) and nearly taking me out through crosswalks lol.

edit: additionally, while i don’t use braille i’ve heard from others that the braille you find in buildings/elevators often isn’t actually legible or functional. just because it’s there doesn’t mean it works.

My problem is that I live in the boonies!

Where to park your tandem!

So we've just got a tandem so we can get into town without having to worry about parking a car.

Cycle parking U racks here are already limited and heavily used so you are usually sharing a rack with someone else's bike, but the kicker is when there is not enough space around the rack for the extra length of a tandem. I can't use some racks because I'll end up with the tandem blocking the pavement or sticking out into the road.

Then heaven help me if it is the kind of rack where a bike is supposed to fit into it.

https://en.wikipedia.org/wiki/Bicycle_parking_rack

Cities are great for us. But just general things. A city that has shitty or unreliable public transportation or is not that walkable ie San Fran or LA are not great cities for VI