Again my questions is, should I be concerned about the current landloard transferring these funds to me?

I know the next thing would be to do a QuitClaim to transfer the investment properties to the LLC. 

This is the precise reason why cash-for-keys is almost always better, especially in Cook County.

These are things you can give in detail to the buyer:Cash flow on businesses, condition of equipment, payroll, more info on liquor license transfer, are there existing liabilities, is the seller willing to sign a non-compete clause in case they want to open another similar establishment or invest in one,  ask about current manager...staff experience, are they willing to stay. 

If I put down 50% and he puts down 50%, where and how do the funds join together and get transferred for the purchase.Once the house is purchased, what costs must be taken into account?

The prior owner's certificates do not transfer to you.

Or are they transferring larger sums from other retirement accounts to get going?

Are there any legal/financial ramifications if I collect rent through my personal Venmo account, then transfer to my business account for my rental property?

He's offering to transfer ownership of it for $500, but I can get a more generic domain for $20.

For instance, Closing fee will be around $1,200Lender's Title will be around $1,000 (or less)Recording fees will be around $140 - Cant say if you will have to pay transfer tax to the City because you have not indicated which suburb the property is in.