Never once seen a baby pigeon, still looking.With Airbnb in Chicago make sure you do your homework on the area, there has been a lot of push back from local governemnt and neighbors forcing restrictions, etc..https://www.dnainfo.com/chicago/20160615/lincoln-park/lincoln-park-being-sold-off-as-airbnb-rental-properties-alderman-says

Trying to do it thru an LLC will make it harder, not easier, as it will still depend on Your credit and the LLC throws in additional restrictions (no conventional loans for one).

You'll have to look at any hoa restrictions and whether or not the rent you would need matches the rents currently achieved in the area.

Interesting that they say "allow anymore" I wonder if they did in the past, and when they might loosen that restriction in the future?

There is so many restrictions around selling property.  

However, if you have a desire to consider other markets that are not as restrictive, i.e.

It doesn't matter what city you're in, ignoring the zoning restrictions is a bad idea especially if you run into altercations with your tenants or neighbors.

@Dean Miller I would add that you should review all governing rules of the association, not just the rental restrictions.

If you have a no smoking policy what you need to restrict yourself to only non smokers.

Assuming I construct fourplex building units would there be any restrictive barriers to sell each building to “house-hack” buyers?