If you win, and they don't move out, you have to go back to court and file for a writ of possession (which costs more money).

I dont intend to go into it till i have most of my cards in my hand.

That takes guts to go up and talk to a previous home owner while carrying guns.  

I'm planning to go out of State as I live in Westchester County NY which is an overpriced market.  

I understand the underwriting procedure and know that even if I can provide the nominal NOI and market CAP rate the buyer needs to go through a much more detailed analysis.

I have no desire to lose money monthly to gamble on appreciation, if I want to gamble I'll buy a lottery ticket.  

I want to pull from my Savings Plan to begin investing but not sure how to go about it looking at my debt to income ratio and having the two property.

Also a “7 bedroom” home may be listed as 4 bedroom on MLS with a “den”, “patio room”, “office” etc. so you really have to go look at the property.

Find a few friends who are at the same level as you, and also find a few who are 2-5 years further along the path that you'd like to go down.

One on hand you want to reach financial independence/retire and/or be able to pay for your son to go to college; on the other, you want to enjoy life and give your family what they want.