They can also ask for longer and are usually granted an extension.I can and do offer cash for keys and it sometimes works but in general I do not get possession until AT LEAST 45 days after the sale.

If not - why not - you need to rent it before settlement - which means you need immediate possession before settlement.

We'll be house-hacking in Chicago, but we're moving out of our current apartment to take possession of the new 2-flat we bought.

Not sure where you are in the process or if that is a possibility, but the preferable way of dealing with this, from your perspective, is for the current owner to get the tenant out before you take possession of the property.

If you are not actually taking possession but bringing a buyer and seller together for a transaction without a license it is a fine line.

I get possession of all things at closing per the contract.

Then, I would guess the Borrower with counsel would seek adverse possession or specific performance on the Fund.

In a judicial foreclosure, the lender takes possession of the property, typically in exchange for extinguishing the borrowers obligations to the lender.  

My goal is to find employment that can utilize the construction versatility I possess.

Yes, renting back is possession after closing, not a good idea, but you can do it, guide you.Your contract can stipulate the area leased, for example, possession of the home and that area within 100 feet of the dwelling or describe it as a legal description as the area to be used.