Because I would have to have the online/cloud version to properly outsource it, which is counter intuitive. 

If the layout of the house doesn't flow, and there's no way to cost effectively reconfigure it, then run away. 

If it is, the fifth bedroom will help you, but it also depends on how big the bedrooms are/ the layout/ the bathroom count.

We changed some of the layout to make it more modern and open feeling all to draw a higher class buyer and it worked.

If the layout was correct for an en suite that would work, but you have to make sure the existing full bath is centrally located.

I seriously doubt TurboTax gets it right - and that is speaking as an ex-Intuit employee.A really good tax person / accountant / CPA is hard to find, but once you find them they will save you huge amounts of time and money. 

I thought of creating a business plan to take to banks that would lay out the NOI to show the last 3 years of actuals and projected 3 years with a bank loan but it sounds like most banks only see this as property not as a business.I know there are many other options with seller financing which *might* be an option.  

That intuition saved us from our entire basement from flooding.

I caught the real estate bug just a few months ago and am now very eager to get started with my first investment deal and looking to hear your opinions on how I should lay out my strategy moving forwardI could write several paragraphs laying out my situation but I decided that it'll probably be easier to read it in a bullet/list form.

Without seeing a sketch its hard to visualize the layout.