Preferences for Neighbourhood Layouts?

Having been to a lot of ports in my seafaring days, in the US of A and overseas, I can vouch for the fact that dock areas are shabby. Not so much because they are poor, but because the whole focus is on getting work done and not on looking pretty. The customer base is largely made up of sailors, folks who are not famous for being either rich or staying there long. Business profits go elsewhere, not the facilities. The only time I've seen dock areas with the fancy stuff mentioned by the OP is when a dock area no longer hosts freighters and fishing boats but has become a marina for rich folks' floating toys. So, yes, that building needs to go elsewhere.

Of the given towns, Windenburg seems the best balanced, though it would be nice to be able to unlock certain places. San Myshuno is a big disappointment, promising so much and delivering almost nothing. The ladies said it well, so won't try to add to it.