Summit County has a severe housing shortage for long term rentals and an overabundance of vacation rentals.

I'm not in Orlando but I am close enough(Lakeland)and I could tell you that there are no real shortages of wholesael deals.

In my opinion (opinions being of little value) and with my experience I have learned that a investors that do not have the stones to weather tenants knowing they are the owner do not have the personal skills or fortitude to be a successful landlord/investor.I never lie to my tenants about being the owner.

That'd be a big deal in terms of ability to manage the work..I'd reiterate that if you want to move forward on a project as you're describing you'll need a good set of A/E plans and some really solid negotiating skills to actively manage the project.

I actually developed some really useful skills in those jobs.

Changes can be made in many areas to help improve your health, your knowledge or your skills.

Find an attorney to help you sharpen your presentation skills. 

Your analysis is missing operating expenses.If gross rent is $1500 assume expenses including management to be 50%So you get $750 per month Before making the mortgage payment.You will have a negative cash flow of (-$650) each month.I would suggest you look at developing your investment skills to recognize a positive cash flow opportunity using your $40k as a downpayment & reserve.  

What you ask is all relative to the project , and desired time of completion , plus your own skills .

I'm planning on talking about the opportunity (size of the market), my skills and why I would be able to bring a unique value to the industry and also how much I need and what I would do with it and how much money I think that I would make in the first year.