I'm on the outside looking in, I've lived in Chicago for 3 years, moved here from Los Angeles (LA), and being from LA, what concerns me is gang violence. You see, recently the Chicago PD have to cut some veterans and replaced them with greener officers, this force then sought out to arrest the leaders of various gangs and cartels. There is now and has been going on a turf war for territory, hence the disproportionately high number of deaths in the black community (blacks make up 30% of the population in Chicago but account for well over 80% of the homicide victims). This, in combination with the school closures and cutting of education funds, has create a perfect storm environment where recruitment into gangs will be an issue. These children will be in overcrowded, underfunded schools, growing up amidst gang violence, likely to fall into a gang, or grow up to live in a city that doesn't have economic opportunities for them.
LA has curbed gang violence by campaigning against recruitment, there's lots of after school programs, community college is essentially free for residents, there's even opportunities for illegal aliens to go to school.
I feel that it will be worse in Chicago before it gets better. Chicago looks big on the map, but you shouldn't go west of Western or south of 38th, that essentially makes Chicago a 3mi x 3mi town. It has high income taxes, sales tax, and absolutely unfair vehicle policies (city stickers, tickets galore, frequent towing).
No city is perfect, but Chicago has a lot of problems for which there are no easy answers. I feel there's parts of the city in decline, there's so many store fronts closed and abandoned buildings, it's like space in Chicago isn't worth investing into. There isn't even funds to put metal signs with red-Xs on the abandoned buildings so firefighters know there isn't anyone inside if it catches fire.
Some parts of the city are growing, but all the numbers point to declining population.
I don't know where I would live, I'm not in a hurry to go back home but I'm not attached to Chicago, I haven't fallen in love with the city the way so many do. Unlike most people, I moved here from a larger city, with comparable (and in many ways better) culture, food, and diversity.
Chicago is a great place if you like Jesus, or dogs, sports, drinking, those are all big over here.
The pension crisis is just one of many things gone wrong here, the parking is owned by a swedish company (for the next 98 years) AND the money that was paid to the city for that is gone, the cta fares are handled by Boeing, schools closing, teachers getting screwed out of pensions.
Oh, and fuck the weather.