If you are on some sort of government program, then state it, don't just say "there is a company that pays that for me." 

Counties reassess property with significantly higher values annually, and local governments assume that they are entitled to a corresponding increase in spending.

However, Black Knight Data & Analytics Executive Vice President Ben Graboske noted the federal government has some buffers in place to block a potential mortgage catastrophe.

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

Assisting the Commonwealth of Puerto Rico and local governments in re-allocating existing federal resources toward disaster relief – HUD's Community Development Block Grant (CDBG) and HOME programs give the State and communities the flexibility to redirect millions of dollars in annual formula funding to address critical needs, including housing and services for disaster victims.

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.

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.