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i expect because doing this means people with bulky items take longer to get through the gateline if regular luggageless folk start going ahead of them, and as a consequence they and their items clog up the concourse more as they wait..... then they decide not to bother going through the regular barriers, the wheely case ends up getting caught in the gateline = even more congestion.
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People who should be using the normal barriers - because they aren't carrying anything - blocking up the one gate I can use because I've got a bike / am wheeling a massive suitcase / whatever is annoying because if you have to use that gate you can't just choose another one.
It's a bit like people who aren't disabled using the disabled loo when there's plenty of others going. Also annoying.
In the spirit of the OP I'll try to keep this to things which might actually have a design solution...
People insisting on using the luggage gates at the station when they don't have any luggage/a bike/a wheelchair.
"Changing villages" at swimming pools. Not just because the phrase itself is an abomination but because they're always horrible to use.
Those stupid ridged things they put in cycle paths where the ridges align with the direction of the path instead of going across it - they can get very slippy.
Noise transmission in Victorian flat conversions.
The fact it's impossible to get a drink of water on the move in the UK without resorting to plastic bottles (and basically what @pastry_bot said, the much wider issue). Not sure there's a design solution to this though because water fountains already exist, there just seems to be a national conspiracy to support the bottled water industry. I have noticed that water fountains are much more common in the U.S.