You are competing with cash guys with those terms. 

When you pick the largest mortgage bank in the country that's known for having "meh" pricing to fund the largest mortgage marketing budget in the country with hundreds of script-reading LOs in cubicles who have all signed (& this is lawful) do-not-compete/do-not-broker agreements, yes commercial financing will be better. heh.If I ever went back to grad school and picked marketing as what I'd study, it would be how a large enough marketing budget can offset almost any other hurdle a business could possibly have, and Quicken Loans would be my case study.

McDougal does seem like a big dog thats doing all the right things there and that'll kind've make it tough to compete.

Dumb questions: if the broker is already a PM, would you be competing with him ? 

The industry keeps hearing a lot of buzz about the biggest real estate player in town - Keller Williams - getting into sanctioning / sponsoring a property management faction of their real estate sales franchise. 

Absent this rule, buyer brokers would be paid by their clients and would compete to be retained by offering a lower commission.The Buyer Broker Commission Rule ensures that price competition among buyer brokers is restrained because the person retaining the buyer broker, the buyer, does not negotiate or pay his or her broker’s commission.

What high-value skills do I need to compete in today's working environment?  

Make lenders compete for your business.

He is knowledgeable, knows the players in Cook County, and is priced very competitively. 

Just wait until he gets a wife and has a kid.You are far from competent my young friend.