I worry about city/government restrictions on short term rentals, but am not familiar with current laws in Chicago.

You'll be able to defer federal however and that would create a net benefit as long as the 1031 didn't cost you an arm and a leg (figure 750 for one).  

Housing and Urban Development today announced HUD will speed federal disaster assistance to the Commonwealth of Puerto Rico and provide support to homeowners and low-income renters forced from their homes due to Hurricane Irma.Yesterday, President Trump issued a major disaster declaration for Culebra and Vieques municipalities.

Go to the county government website for the county where the property is located. 

The numbers being audited by the government are Dave's...not the CPAs.

In a large minority of cases, the tenant pays both agents.There's no strict guideline and the commission arrangements are certainly not governed by law, except that any commissions paid by the tenant must be disclosed in writing and have the tenant's signature approving it.If you rent it yourself and have signed an "Exclusive Right To Rent" agreement with your agent, you will still owe the commission.As an aside, I try very hard to stay away from rentals.  

He sounds like his strategy would work well for you.I'd hate to see you sell this one then have to pay 20-35% back (depending on your tax bracket) to the government.

It has saved me at least $1,200 a year in federal taxes for the last 5 years.

@Phillip Lirette can also try credit unions: Riverland Federal, ASI Federal, and Campus Credit (the last two both do significant business with Small Businesses).

Since the government has such huge expenses after a situation such as this and the majority of tax payers end up on the hook for the costs is it appropriate to allow any one to rebuild in a area that will inevitably be devastated over and over again.