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.

My current HSA allows me to invest in mutual funds.

I can see how it may be mutually beneficial.