You will want to review these as soon as you get them.

You will likely only need an attorney to review your purchase contract (unless you use your own and the seller agrees, then you know exactly what is in it). 

You could use VRBO etc  but the reviews can derail the process. you have work extra hard to make the guests "happy" .

I would double check your contract and any you review into the future.

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Honestly you really need to work with an insurance agent to see if they’re gonna be there for you when something happens so reviews are key.Same thing with a realtor.

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I'm not an attorney nor do I feel like you need them as much as people think but in this case, please invest a few hundred bucks into a professional contract that is reviewed by a real estate attorney in your state.

So contact everyone :)One of my recommendations would be to contact the source who would review the work at the City of Chicago.

Of the scenarios you list only 1 and 3 make sense to review.