And he does make a fine wine.

In some municipalities they require both a preliminary plan and a final plan, effectively making you go through the approval cycle TWICE. 

I'm in a final round with a company but steady income has not been secured yet so if I could at least cash flow that would really help me stay afloat for the time being.Obviously I could market the unit as-is and potentially rent to someone but won't likely be able to rent to a section 8 tenant which I was hoping for down the line.I was considering starting off with 3-month leases with auto renew and I have been VERY clear with him that if he is unwilling to pay on time that I still am treating this as a business and am not afraid to evict him.

Very key thing here, I don't have a finance/economics background, and am just getting started in this area, but this struck me as a good strategy to use.

Consider the time, effort, and expense to develop a concept plan to include site drawings, home types, homes per acre, site storm water retention plan, tree save areas, conservation areas, wetland setbacks, time considerations for meetings with county land use planners, negotiating easements for utilities, rezoning meetings with county council, revisions to your plans to meet demands of neighbors, planners and/or county council, and hopefully getting a final approval for your project.

I did a few and someone turned me in :) and sure enough I got a cease and desist and had to pay a fine and spend 20k creating what State of Oregon  calls a Real Estate paper offering !!.  

So its a fine line on how to balance those things and grow whatever business you want to grow..

My wife is CFO at a Finance Institution.

It's a fine balance between economy and what you would do for oneself, but creating a space that feels like home should be of primary focus.If you're looking for some insight into re-leveraging any investment properties for capital improvements, furnishings, etc, some lenders can utilize AirDnA projections to qualify. 

An attorney for a final peek is always a great idea just to ensure you are covered.