Thank you for taking the time to thoroughly outline a real life comparison you experienced @K S.

Get the book "Deals on Wheels" by Lonnie Scruggs and it outlines a plan of attack for this type of investing.

(LOL)Run this by your attorney/mortgage originator, remember the SAFE Act, the note terms outlined will meet those requirements.

The bill outlines an audit process for buildings, but doesn't require those audits except for new construction and some commercial buildings.

In this 10-part blog post - spread out over 5 weeks, I will outline, in broad strokes, the 5 ways of selling houses FAST in this really slow real estate market.What is TIP # 1?

However I never saw Brandon outline taxes (specifically for income, not property).

My recommendation would be to link up with a licensed realtor in Connecticut that knows the different markets and can breakdown for you what to expect in the different areas you have outlined.

Running the numbers: Before you do the rehab, I would put together an Excel sheet outlining the cost of the rehab, the expected additional rent, and the lifespan of the renovations.

Instead of a BP tax expert trying to outline all the different scenarios, in a half hour or so sit down a CPA could give you an awesome broad-stroke 'what-if' for you. 

Free option - Get a copy of an old survey from the county showing easements and setbacks etc and sketching the outline drawing of the intended build on the survey.