It is a family friend and they are looking to sell, it needs a major rehab on the entire property but my wife likes the location(about a block from our pastor’s house) and in the school district she teaches in.

If so, what should I do as far as an addendum or extension to the contract?  

I would look up the laws surrounding storage units in your location and then follow those.

Let me know if you are still in need of services to help you locate your Home

And depending on how he deals with them (whether he tries to handle the claim himself, or hire a Public Adjuster, which I recommend), settlement amount can range drastically.Depending on the extensiveness of the damage, most of the time, Public Adjusters are looking out for the insured's best interest, since they work on a percentage of the proceeds, so they'll point things that need to be remedied to the insurance company, that the homeowner will have no clue about.

This property is located in the hottest neighborhood in Chicago so if I sold it I could sell for a 75k profit or if I rented it out I could make $400/mo doing so.

Can you tell me best locations to flip houses?

I like Bucks county a lot, but not too sure about best multi-family locations.

(reasons to file multiple - property is located in a different state or you work in a state other than the one you live in)Is the LLC a disregarded entity or does it require the filing of a partnership return?

Rent is hyper sensitive to locations within an area.