Based on these factors (and the fact that I am new and would prefer cash now to do more deals) I am leaning towards flipping the home.Thanks again. 

My plan is to milk this cash cow forever, do $40k cash out refi in 6 mouths, use the money to purchase multi family properties.

It's all factored into the contractor's bid.

Prices will reflect that, but buying dirt cheap means selling dirt cheap in a small town that isn't "related" to a larger market.Study real estate basics, location, market influences, inventory turn over, economic factors that effect value.

The goal isn't to live forever, the goal is to create something that will!"

The biggest factor in the financing is the cash flow.

Lenders are going to take all factors into account including income, marital status, credit, etc. and through the rate they give you they are telling you what kind of risk you are to them.

Any clarity on this would be much appreicated, In the future I would like to be an out of state/city landlord (as I really don't plan on staying in NYC forever) so any one with experience in this, I would be really grateful to hear what you have to say. 

Is broker support always a huge factor?

My 2 cents would be that you may not want to work under the same broker forever.