Our original flood insurance quote was $4200 and after an elevation certificate from the surveyor, it is now approximate $1200 I am sure someone will come along here behind me and have more beneficial info, but just wanted to add my 2 cents.

Are you suggesting that it may be more beneficial to rent it without finishing the basement?

Word of mouth can be very beneficial.

As I live in FL and am a complete newbie, i'm looking for someone to partner with and hopefully work out a mutual beneficial strategy with some of these properties. 

The questions, then, are how could I present this to a seller effectively to where we both agree that it’s mutually beneficial and is this a reasonable strategy in hot markets where house prices are far outpacing rents (we are obviously no where near the 1% rule)?

They do not provide such services, and have every incentive for you to NOT look into such a plan which will deprive them of the commissions they receive for selling you stocks and mutual funds. 

My accountant told me to switch from a single to multi member llc for beneficial tax purposes.I was planning on adding my wife.

I think it could be beneficial to show her the numbers.

It would be beneficial to know if any big corporations or businesses coming to Chicago??

You would then later assign the beneficial interest to your LLC.