Will the contractor have to do other jobs simultaneously in order to keep food on his table? 

Job insecure, food, medicine, transportation insecure ~ and the first thing they need to give up is rent in times of crisis.  

For now, it's better for me to live downtown where all the action is (investors, capital, startups, food, entertainment, walkability). 

How about an REO with a property preservation team that left a fridge full of food and a standing freezer full of food in the house for more than 18 months?

My opinion only....food for thought.I know nothing of your current job, but I would recommend keeping steady employment until you have a solid #2 going.  

Most important, I will be sampling copious amount of alcohol, food, tea, events, and nightlife.If someone wants to join me in any of the above endeavours, talk some real estate, have a beer, etc. it's my treat.

Had I hit the next tier (16 loans) my pay would have jumped up to about $14k lol and I only worked 5 days a week, 10 hours a day with ALL food paid for. 

Hey Realtyman go look on the back of the packages of foods you eat and you'll more likely see an LLC there.LLC's aren't evil.

Just some food for thought.

Thanks to what I had learned from this experience and the confidence I developed I was able to continue flipping houses but this time in order to put food on the table.