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.
Many US states got their capital chosen because when the territory became a state it happened to be the closest to the centre of population of the state. Jefferson City, MO is a good example of this. The three major population centres at the time were St. Louis, Kansas City and (to a much lesser extent) Joplin. So Jefferson City was right by the centre of population.
Meanwhile, most European capitals (including at the provincial level - think German states or French regions) came to their state by being the capitals and cultural centres of feudal states, which gives them more depth.
I don’t mean any offense to Iowa (this time), but there’s not a huge amount going on there. It exists almost exclusively as an administrative division.