In addition, flipping house can be an awful experience...I've done it in my day job several times and I can honestly say that I would not want to go through both sides of the flipping process (buyer and fixer), which is how I would tackle the project.

Sat on it for almost a year trying to work up the courage to tackle this massive piece of rework.

But I believe I am ready now to tackle a flip.

The simplest way to achieve what you want is to purchase the property subject-to the existing mortgage.That said, there's a decent amount of training and paperwork you'll want in place before tackling such a transaction.

However I’m wondering if that will be a mistake as by the time I’m done pretty much everything will be done with the house, new HVAC (unplanned) and huge trees being trimmed to name a couple big items I planned to tackle down the road.

Now that you have divide and conquer your task list it is much easier to tackle the workload . . .

Patience, a willingness to tackle some deferred maintenance, and a realistic expectation of pricing can help.

A D/F areas are really towards the advanced level of RE and should definitely be tackled by experienced folks whose business revolves around the benefits and challenges of that type of real estate. 

I'm not familiar with the NYC market however I'm happy to try and tackle any upstate investing questions you might have.

I would look at all possible uses and tackle my network to find out who they know.