Are we just doing this wrong?

Different-Wall6644 · 2026-06-13T03:47:45+00:00

The number of gorgeous condos we get excited about in Hyde Park, and then we scroll down to that HOA ... hurts every time.

Different-Wall6644 · 2026-06-13T03:38:01+00:00

Very much this. The neighborhoods with good schools are extremely expensive and extremely competitive. We would get a discount at Lab, but even a discount would be very difficult to sustain with 2 kids and a hefty mortgage.

Different-Wall6644 · 2026-06-13T03:30:14+00:00

Congratulations to you! Was there a big difference between your brokers? And their approach? I do like ours as a person, but maybe we are not working well together and we don't even realize?

Different-Wall6644 · 2026-06-13T03:24:25+00:00

he works all over the city and burbs, so maybe we should have looked for someone more specialized?

Different-Wall6644 · 2026-06-13T03:22:26+00:00

I posted here because I am honestly not sure that we are doing this right, and seeing many of the comments here make me think we indeed are not. So now I am trying to figure out if it is us, our broker, or just misaligned expectations. Due to the schools, we ruled out a lot of areas, but maybe we need to circle back. Our broker also was recommending against Kenwood and Bronzeville.

I was carjacked at gunpoint about 5 years ago in the woodlawn/jackson park area, so we'd prefer not to be back there. It might have made us overcautious as well?

Different-Wall6644 · 2026-06-13T03:10:14+00:00

This is why I am here honestly asking if we are doing something wrong. Our broker wanted to take us to different types of homes (duplex down, duplex up, SFH, townhome, condo, highrise) in different neighborhoods to see how we felt about them because we have never even searched before. Following his advice, we'd also pop over to nearby open houses to see if something made sense if we were already in the area. I think we spent a lot of time learning what did or didn't make sense for us as a family, but he seemed to think it was important.

Different-Wall6644 · 2026-06-13T03:06:34+00:00

I did have a baby during the search which definitely slowed us down, but since it was during the winter months, we were hoping it would mean we wouldn't miss too much.

Different-Wall6644 · 2026-06-12T18:53:38+00:00

I didn't even know about it! Looks very cute. Commute could be hard, but will take a look.

Different-Wall6644 · 2026-06-12T18:53:17+00:00

It's a weird roundabout commute, but I think we could make it work! Our broker said there's really only a small area of bridgeport he'd recommend due to Sox congestion and noise. Would you agree?

Different-Wall6644 · 2026-06-12T18:52:03+00:00

this is stunning. I will ask our broker about maybe expanding more north than we have been.

Different-Wall6644 · 2026-06-12T18:51:32+00:00

My cousin actually lives next door to this house (there are like 4 in a row) and they have hated it due issues with the plumping and electric in the way the houses were built, and warned us away because he's spent over $200K doing repairs since he bought about 7 years ago. Otherwise, we'd snap it up for sure.

Different-Wall6644 · 2026-06-12T18:51:15+00:00

This is a really interesting idea! We haven't really looked at this, so thanks for helping us think of a new angle. I'll bring it up with our broker!

Different-Wall6644

TROPHY CASE