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I open the first one.

Nothing.

The second is more promising, but there is an unresolved zoning issue that would require significant work. I flag it cautiously.

The third property makes me stop.

I know the address before I finish reading it.

Diego’s old apartment building.

I sit up a little straighter and open the file fully.

There it is: the converted warehouse near the river where he lived before the structural evacuation forced him out. Conti Enterprises had tried to buy it twice, exactly as Diego told me when we first started working together. Both offers had been rejected.

I remember him mentioning it almost casually, like the failed purchase was simply another deal that had not worked out.

At the time, I had been more interested in finding him somewhere else to live.

Now I am looking at the property as part of an acquisition review.

Interesting.

I start with the basics.

The building itself is exactly what I remember from the limited information I had when Diego first contacted Meridian: luxury conversion, large units, exposed brick, high ceilings, terraces, underground parking. The structural issue is noted in the most recent records, along with the evacuation order and ongoing assessment.

That part does not surprise me.

The ownership history does.

The building is held through an LLC, which is hardly unusual. Half the commercial property in Chicago seems to be held through one LLC or another, and anyone who has worked in real estate for more than five minutes stops finding that remarkable.

Still, I open the ownership records.

Then the prior transfer.

Then another.

I pull up the financing history and compare the names.

Nothing immediately jumps out as wrong, but the structure is more layered than I expected for a single residential building. There are entities behind entities, financing arrangements that changed even when the property itself did not, and a couple of transfers that make me pause long enough to reread the dates.

It could mean absolutely nothing.

Complicated ownership is not the same thing as suspicious ownership.

I know that better than most people.

I add the building to the review folder anyway.

Not because I think I have discovered anything, but because Conti Enterprises already wanted it badly enough to make two offers. If the structural problem can be corrected and the current owners become more receptive, there may still be an opportunity there.

I type a short note beneath the file.

Revisit after structural assessment. Ownership history more layered than expected; worth reviewing pending another approach.

Then I move on.