But if you are not cautious, well.....

He's very active and knows the market quite well.

For me at least, doubling my profit is well worth the extra two months of expenses on the market.

First time investor, hoping to obtain my first duplex soon, and this family land purchase is on the horizon as well.

Even if you only averaged 2.8% appreciation annually, which if you've had it 20 years I have no clue how that's true given prices have well more than doubled in that time, youre skipping over the fact that you have been benefiting from that appreciation on the ENTIRE house, not just the % you paid for.  

Being a NYC resident (originally from Long Island), the price of entry in the area is on the higher end, so I've been considering some options in the NY Capitol region, as well as NJ and CT. 

I have a call out to my accountant as well. :)

Well duh, because that motive to alleviate the bad is gone. 

Those remote flips and high cash flow rentals are so tempting on paper, but they rarely go well in reality. 

I'd look at that as well as the Zoning Ordinance and Subdivision Ordinance, which every Pa township, borough or city has, or if they don't have those docs, they are covered by the county codes.