From there we used our savings to slowly buy other houses investments and than when we were transferred personals.

Here they are:1.Identifying YOUR goals2.Identifying the client’s problem (s)3.Providing solutions4.Handling Objections5.Asking for the CloseIn the investing world, “Identifying your goals” typically transfers into profit margin.

I'm looking for an online resource that has data on average cash on cash returns for multi family investments in a given area.  

I would also suggest you call up a title company and get a list of recent property transfers.

Here is how the ROBS 401k business funding arrangement works:A new C-corporation is established.Corporation sponsors a new 401k/PSP.The IRA funds are transferred to a new brokerage account opened for the 401k/PSP.The new real-estate operating company corporation issues stock shares to the 401k/PSP.The real-estate operating company must be an employee of the business and he or she may take a reasonable salary.The business owner's family members may be employees of the business and receive reasonable compensation for their services.To the extent that the corporation generates profits and elects to distribute those profits to the owners of the business, the percentage of the profits associated with the shares held in the 401k/PSP will flow back to the 401k/PSP brokerage account.

I don't really want to risk the due on sales clause resulting from a subject-to transfer, and getting a hard money loan to buy the house outright seems like a waste if i can instead setup some type of joint venture. 

We will transfer the property to an llc.

Hello BP, i plan to have the seller transfer his property title to me and then i find a buyer for a "Wrap Around" mortgage transaction.

If data show approaching that top again for your area you might want to change your plan.

what data or report did you read the cities you have mentioned have had larger appreciation then Chicago?