Both have positives and negatives that make each more, or less appealing than the other. 

Cash-flow positive Lessons learned?

I wouldn't give too much thought to his financial position, because it could go any way; he might be a billionaire because he's a shrewd negotiator and enjoys pushing back, and at this point, he doesn't NEED to sell.

Since I got out of the military, I had various positions, to include selling security systems with ADT. 

What can be done with these types of leads: highly motivated seller with a low-equity position?  

Providence and surrounding neighborhoods don't have positive inflation-adjusted growth over the long-term (shocking) so to make money in this city you need to i) invest cyclically and ii) have access to good deal flow.

Majority of folks around here would do anything to be in your position. 

My plan is to rent it for 1450 to 1550 a month (average rent in the area) and I should have about a 45k equity position at least. 

I basically live a boring life (for now) and it's not the best but I will deal with it for a few years to get myself in a better position as this allows me to save over 60% of my income annually. 

I read on the forums about other folks purchasing properties for much cheaper and making them cash flow positive.