My pick is Des Moines, currently living here. Like, there's almost nothing worthwhile to see and there are pathetically few skyscrapers. I live in an area where I can get a good picture view of all of the buildings within sight.

And all I can feel is "...there should be more". The buildings themselves aren't even that interesting. Des Moines tries to make itself feel big and comparative to other cities, but it just cannot do that.

My other pick is Montpelier in VT, where I have also lived. Everything feels too damn clustered. the neighborhoods are on steep ass hills with awkward traffic markings. There's almost zero reason to really do anything there and it can easily be missed. Like, you can drive from Barre and through Montpelier before you know you're on the highway out of Montpelier.