It only gets better with seasoning.

@Ned Carey  I can agree that price to rent ratio will indicate an immediate lower cash flow and should be considered by a novice investor but any seasoned INVESTOR should understand leverage/overleverage and that cash flow OVER TIME and appreciation is the true indicator of PROFITABILITY. 

Brandon, if you're working with a seasoned investor he won't mind paying you an assignment fee.

Simple green space and seasonal food vending in the heart of town would seem to be a fine plan, entirely within the zoning ordinances as they currently exist (although a restroom facility may be necessary for long term).  

I currently am getting $675 a month positive cash on my paid for rental and would like to receive at least $300 a month on future properties that are financed.My question is, what would be the best way to leverage this property and will the lender consider me a seasoned investor and work with me ?

In my experience companies get specifically touchy about this subject during hurricane season.

Your management costs are greater (25-50%) if you have it managed, And your window for income generation is often seasonal.  

Im a young new investor in the DMV area who is currently seeking any seasoned investors looking for assistance in their flips.

It is difficult to tell how new or seasoned the loan is and how the loan was performing prior to your purchase.  

Tip: never expect to get much done during deer hunting season.