What neighborhood of Chicago and how large are the buildings?

Here’s the context:The house appears vacant, with a large tree that has fallen on the property.From what I can see, the house seems full of furniture and might even be a hoarder home.I’ve skip-traced the property and found that the owner has unfortunately passed away.The house seems to be mortgage-free, and I’ve identified three phone numbers associated with the son, who I believe is the heir.I’d like to reach out to the son to express my interest in purchasing the property, but I want to ensure I do so respectfully while also gathering the right information.Here are my questions:What’s the best way to approach the heir while showing my condolences for their loss?

Direct mail, SMS, door knocking, Facebook ads?"

He strongly discouraged adding a backwater preventer bc he said he's seen it make things worse.

The Due On Sale clause was added I think in the 1980s because of "sub-to" deals.

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My underwriting would have this large negative cash flow for 7 years.I would do a thorough underwriting but want to show using quick math the issue so I will use the 50% rule.  

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

You already live on the property and would be adding three more unrelated people, which is not allowed.Here's a link to the actual code:https://online.encodeplus.com/regs/orem-ut/doc-view.aspx?

Maybe adding a camper spot as well?