I narrowed my search to Kansas City, MO as the location in the midwest I would have the best chance of getting the benefits of cash flow and appreciation in comparison to the NY market.

On the conv-95 you mentioned, chances are good that MIP falls off at 75-80%LTV without the need to refi, but you'd want to double check that with the lender. 

I know that the longer the rental income history the better chance I will have.

If it doesn't sell at $790k yet is relisted at $950k, chances are the seller doesn't care whether or not it sells.

You’re 18, get out there, take chances, and go for it!  

and a 51% chance they will be at 0.00% in April.

Chances are quite high (unless you're targeting divorces) that they are living at the same address. 

Windsor is a great "small town" that generates good cashflow with moderate chances of appreciation (relative to the CT Market)Granby even a smaller town feel than Windsor, rentals are in high demand and rent prices are high.

Chances are that you'll have to get an experienced partner on board.

This was you have up to an chance to see properties up to a week before they hit the market.