New Yorker trying to get started anywhere but New York

[Aaron Rosenberg]

Hello BiggerPockets,

My name is Aaron and I live in New York City, a place where $1.5 million gets you a box built in 1925.  I am not making either of those numbers up.  The high cost of entry to both real estate and personal home ownership has been a thorn in my side for life.  

I do not have any experience in real estate at all.  Since I'm eager to make my first deal this is probably a bad thing.  Here's what I do have:

• Ethics: I want to create a good home for a deserving tenant...in exchange for positive cash flow.  No nonsense.
• Risk Aversion: I will not spend THAT much money that I don't have right now.  
• A job: If there are no tenants I should be able to pay the property's needs myself if necessary.
• Loyalty: I am slow to act because I am a friend for life.  I will buy and hold not for want of appreciation but to keep someone's home in good repair and eventually enjoy a cash flow untainted by mortgage payments.  (Just a cap rate.)
• Crazy Math Skills: I teach advanced algebra.  I have zero fear of numbers, equations, and spreadsheets.  I hunt down solutions for fun and there are few that can hide from me.  

I've looked into a real estate book here and there in the past and decided to get back into it on the discovery that I don't HAVE to own property where I live.  I'm looking at Hartford CT right now because I do successful business there and the food is to die for.  As much as I love the town I'm not married to it--the blog posts here suggest that would be silly.  So I'll buy where it's smart to buy, but...

...how do you know where it's smart to buy?
...what about a town should you look up before you buy there?  

...where do you go to find these nebulous "market conditions" articles always mention but never go into how to analyze them?  

See?  No experience.  I'm all questions and dreams.