The nature of real estate is changing, and Chicago is going to have to adopt to this. With taxes and fees on the rise, and with the crushing pension obligation, you're going to swing and miss if you keep going after homeowners.
I've read articles about a slew of companies leasing up apartments in apt buildings in the city and then subleasing out rooms for short term rentals. This isn't an AirBnb concept, its short term rentals for a few months or up to a year for people doing work in Chicago and then moving on.
In a building I own in Lakeview, an entity wanted to lease up one of my garden apts and sublease it as an AirBnb, saying they would handle all of the licensing, etc. I politely declined.
Another company now wants to do a corporate rental of one my apts in a Bucktown building. They will sign the master lease and then bring employees in for short term use as they do work in the city. I was not getting these types of offers in previous years.
The city is going to need to get more creative to get its revenue. It's going to have to relax its rules with AirBnb rentals, too. If you don't want to piss off homeowners (and hence voters), you need to open up regulations a bit.
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