Stop with the comparisons already. Each city is different. Location, taxes, employee education and skills, and much, much more may explain why some cities do better than others. If all these cities are so great, feel free to move there. Besides, if you lived there, you would understand that they have their problems too. You just don't see it on a visit.
I get people's frustrations with New Yorkers because nothing is ever "like New York", however, in Jacksonville's case, there needs to be MORE bitching and less "move away if you don't like it".
Milwaukee is a great town. I get to go every 1-2 years to visit friends and I always have a good time and leave feeling impressed. It's freakin Milwaukee. If that town can thrive and make a person feel all warm inside, there is NO excuse why Jacksonville cannot. The attitude of the people in Jax is that Jax is ok, and they are fine with that. Well, then shoot, I guess if everyone is fine with the way things are! I personally was not, so rather than try to fight the impossible battle (5,000 citizens who want better versus the other 1.4 million, lol), I left (not to mention, I wanted a top notch education and a place where I could find ladder climbing career opportunities and challenges not available in towns like Jax).
The big difference between a city like Milwaukee and Jax is that the hometown pride of Milwaukee's citizens leaves them clamoring to come together to make the city a better place to compete in a new age where manufacturing has left many of Milwaukee's peers high and dry. Citizens in Milwaukee recognize that quality of life is the most important aspect of a city, and will retain human capital and the firms chasing that human capital. The citizens seem well traveled and well versed in what makes a city tick and succeed. So they make sure their parks are maintained (and their parks are GREAT). They have bike trails that are very very well maintained - I bike along the lake from my friend's place to south of the museum, which is also a great architectural statement for such a small city. The institutions there are well funded and important to the citizenry. The city is hell bent on maintaining functional urban neighborhoods, and heck, the Third Ward is literally all empty nesters who WANT to move in from the western suburbs once their kids are grown.
But my experience as well is that the Midwesterners up in Milwaukee are also far more traveled, better educated, and generally wiser than their counterparts in Jax/FL. Sad to say, but it's true in stats, evident in conversation, and apparent just by visiting their fine city.