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You mentioned the OP should pick Milwaukee because they had a lot of outdoor activities and down to earth people. Well Houston definitely has a lot of outdoor activities so that only leaves......well you get where I'm going.
I know that's not what you meant. Just having a little fun with it.
Of course Houston has those things, I just thought that the OP would do better picking Milwaukee for those things.
I am surprised by the advice on this thread. Houston is fifty miles from the Gulf of Mexico, and while the Texas coast is pretty ugly until you get down to South Padre, the reason it is ugly is because the silt from the Mississippi flows west which means you have some of the most nutrient rich salt water in the western hemisphere. Fishing on the Texas gulf coast is spectacular and is in an entirely different league to fishing in Lake Michigan. Just ask the pelicans. You can swim, sail, fish from Houston year round. For year round outdoor activities Houston is way better than Milwaukee. Plus it is a much larger and more diverse city with MUCH better restaurants, universities, cultural amenities of every kind, theatre, fine arts, music etc. To get anything equivalent in Milwaukee you would have to drive to Chicago. In Houston, you also have to drive, most of it is pedestrian unfriendly, but you don't have to drive to a whole other city. I would rather live in Chicago than Houston (except for November to April), but Houston has quite a lot more going on than Milwaukee at around the same price if not cheaper. Houston in a no brainer.