We already have 1-5+ bins per building, because that's how many bins already go out, with some folks having to put out 2-3 bins for a single dwelling unit. The increase in size might actually decrease the amount of bins and space they take up on the curb/easement, and unless people are putting them in the street they won't block any parking. People should also already know where the cars typically end up parking, and as long as there's enough space to get the bins through it should be no issue (which I agree could be an issue unless we go with the opposite sides method NYC uses which I think we should do regardless).

Bins also are typically not picked up directly from the sidewalk, they have to be brought to the side of the truck, the truck arms usually can't reach more than a couple feet from the side of the truck they are on, they're not telescoping/extendable usually.

As you say trash day isn't the same across the city, no city could operate that way, so bringing this up is a moot-point, we already have bins and bags out as a part of existing as a city.

Wheel-bins size and weight on their own are far more likely to stay put than the small 'have to lift them' bins that we currently have.

I do however agree we need a far more robust street sweeping schedule, which would be best implemented with opposite sides rules, ex. the day after trash day is one side of the street, and folks aren't allowed to park on that side, then the following day is the opposing side of the street. Even if that was done once a month on side streets it would be massively benificial to reduce refuse accumulation, and general road debris like leaves, sticks from storms. (this would also be a great option for snow cleanup/widening roads)