It normally puts all of my cash back into my pocket in a 10 year span after all expenses and what not, however I am yet to carry a single family rental for even 5 years.

I'm currently looking at my third property in the span of 4 months and was worried that I was moving too fast.

Price was higher than laminate, but we are looking at the durability, longer life span and savings that will come over time.  

I have the attention span of a gnat.

I don't use cap rates to calculate as they don't really mean anything to me, more than the amount of $$ in my pocket at the end of the month.Areas span from equity down to income and clientele certainly changes with that.

That is where you can usually unlock value and big gains for your time.You were very lucky as any market across the country can drastically change in a span of 16 months.

So if you live in one of the 4 units you can exempt the relative amount (1/4) if you live in two units (2 years in one then 2 years in another) over a 5 year span then you can benefit from 1/2 of the  capital gains exemption as a function of.

The Marlboro area is a great area with mid-high middle class workers, while Freehold spans from lower to upper (make sure to study market before jumping in).  

Question: how many times and what time span is sufficient to go back to re-offer whether the same $$$ or slightly higher to the seller.

One problem with 'nicer' neighborhoods/properties ESP NYC is that your competing with investors with different motivations bidding up the price.You have investors with money just looking for capital preservation and growth, they might not ever NEED any cash in their entire lifetime so they can buy in solid NYC neighborhoods knowing that in a long term span the price will at some point go up.