"Flip" to buyer at price based on comparable comps in the proximity of the new buildTo me this could be done in a way where it could potentially be a double close if I am efficient enough.Is anyone familiar with this, and is there anything that I might not be thinking of that could be detrimental to this strategy? 

They are looking at comparables from six months ago in many cases, which can hold value down. 

If you sell in 1-2 years take into account the market could swing, in a market like yours(OR) the prices can change quickly compared to a Midwest market. 

And this would satisfy at least one tax court ruling out there.Just be able to look yourself in the mirror and have a good rationale for "changing your intent". 

I know this is a different approach compared to maybe saving money over time to invest or, even something wholesaling or flipping.

Though I have a promissory note and a recorded second mortgage, the current value of the property is not sufficient to satisfy the first lien holder and my loan, therefore foreclosure will result in locking in my loss.What options, if any do I have to recoup this six figure loss?

If not, the $250 is still a sunk cost so forget about that part - you're comparing $700 to the cost of a new system.

@Bill Brandt first, if you are using year ago data to compare, you will certainly miss the turn and only identify the shift in the market in the past not in the present.

@Bryan Milian1- One month of market research on major metro areas2- Two weeks of talking to leading agents in your top 3 markets3- Four weeks of learning the markets4- Offer, offer, offer- stick to fundamentals...long-term buy-and hold small MF (your available cash will be the number one factor in determining what you can afford and what locations you will end up buying in...you'll be comparing apples to apples in your top 3 markets...as long as you have a top agent, you'll be golden)Best of luck 

I can say from regent experience that there is plenty of demand for rentals in Lowell and rents are pretty high compared to purchase prices.