So with such radical change, the players and there intentions too have radically changed and morphed over time. 

On the flip side of that axis, high appreciation properties often generate cash relatively "poorly" as they are in limited supply areas (like a peninsula or an island or a ski resort) and more and more buyer types want to own them and are willing to "overpay" and ignore rental production potential.

From what I've been told, realtors often come with high recommendations to their clients for other team players (contractors, inspectors, lawyers, etc). #2 Should I still vet these recommended team players before signing any contracts?

As a contractor, sometimes I want to show how much I charge to a client so they could understand, if in case the seller won't get it, your last resort is to show them all the costs and estimates and how much you want to make, remember this is  "Last Resort Only" option where after that move, you lose the deal.

This would be the last resort as I don't want to pay a 5% PPP, nor do I want to wait 5 years to buy my second property.

So I resorted to your same 'old cable' run routine. 

I know I have lent to many over the years.. there are for sure smaller players doing the flip stuff...

They're worried about bad players doing bad work. 

Who are the major players in the Chicago multifamily market?

This would be the last resort as I don't want to pay a 5% PPP, nor do I want to wait 5 years to buy my second property.