Apparently a measure to mitigate re/building in high-risk areas?

You can't avoid that, but a good mentor/partners/coach can mitigate it.

While it is also true that Chicago leans tenant friendly, you can mitigate a lot of that risk by investing in areas that have a stronger tenant base.

I have a secondary residence home insurance on this house and getting claim back for the mitigation/repair work.I have this house on Airbnb for short term rental.

If you balance the portfolio with say 80% cash flow positive and 20% on the extreme ends, you'll mitigate the risk of losing your shirt should the prices drop as your portfolio will be self sustaining. 

But inexpensive and will mitigate your risk.

While there are indeed risks associated with syndication investments, prudent investors can mitigate these risks through proper research, diversification, and working with reputable syndicators who prioritize transparency and alignment of interests with their investors.Ultimately, while syndication may not be the right fit for every investor, dismissing it outright as not "real estate investing" oversimplifies a complex investment strategy and overlooks its potential benefits when executed responsibly.

Flipping is always risky business, but if the numbers work and you work well, you can mitigate your risks and turn a great profit…even in this market.

This could be great for you as who knows better than a company managing other units in that market.However if mitigating cost is a big focus, then like mentioned previously having someone you know and trust is key.

Risk Mitigation: Risk is shared among partners, reducing the financial burden on individuals in case a project doesn't yield the expected returns or in the event that the costs for a project end up higher than initially planned.