While we enjoyed living in a downtown condominium, we've found living in a single family home in the city to be much more suitable. You may find this to be so, as well.
Three years ago my wife and I moved back to Chicago from northern California (yes, "northern," as in Humboldt County, which is "northern"). After living in single family homes for most of our adult lives we thought it would be a good experience to live in a condo downtown. Less responsibility. Someone helping you with groceries, answering the door, no snow shoveling, or taking care of a yard, the trash receptacle only steps away.
We opted for the South Loop because for condo living, that's one of the best values. Close enough to the Loop, Michigan Avenue shopping, and even River North for walking. Tremendous access to Grant Park, Millennium Park, the Museum Campus, the bike trail. That's all really good, and enjoyable. And, we had a wonderful view of the amazing skyline and summer fireworks at Navy Pier. But, like anything that is easy to take for granted, the novelty wears off eventually and you get real.
Condo living is not always as easy as it seems. First and foremost, don't get on a condo Board of Directors. Secondly, be willing to accept that everyone is different, especially in their expectations. If you think "entitlement" is a macro problem in our country, and a micro problem in your family, wait until you encounter the spoiled brats in a condo high rise. It's a shit show. One clue. Live in a building where the average cost of the condos are relatively the same. Don't buy in a place where a million or millions of dollars separate the owners. There will be costs when you share the amenities of a building. And everyone pays. But, those who squeezed their budget to get in the building will fight tooth and nail against the additional cost of upgrades, repairs, and new amenities, even when absolutely necessary. Finally, we found our building, relatively new construction, to be fairly quiet inside. But, living in an area such as the South Loop, highly concentrated with road and foot traffic, can be painfully noisy at times (honking, motorcycles). Sound travels up, trust me.
So, we moved once more to a single family home on the north side. Privacy. A yard where we can have our own garden, which we missed. No concern about annoying someone upstairs or downstairs, or them annoying you. Not having to wait for an elevator to get to the garage. Or dogs pissing in the elevator and the owner or dog walker leaving the mess. Running into someone on the elevator when it's not their day. Or yours. Not being scared to death an upstairs neighbor might leave a window open when it's freezing cold outside, leading to a frozen pipe burst, causing a flood that destroys your wall, the floor, and your furniture.
Yes, now I have to shovel snow, which I swore I would never again do. I take the garbage out and put the large container in the alley. I'll be gardening soon. Yay! And we live in a nice neighborhood with trees and friendly folks all around, and families, with little library boxes every couple blocks, and mail boxes. It's not always quiet, but it's much quieter and actually less stressful. I drive a little more, but I've figured out that getting downtown when you live in the city is actually pretty easy, and it beats taking a taxi anyway. And the "El" is my friend. Our access to restaurants and shops is great and better than where we were. It's also pretty clear to me that the value of living in a single family home in Chicago is quite higher than a downtown condo.
You learn to live with anything when happiness is your goal. You overlook the manageable nuisances, such as mentioned above, and be grateful. Maybe none of those things bother you. But, they're all things you don't think about when you're entering that Life Stage.
I'll get back to you someday and let you know how this one is going.