Is this typical?

Yes, but you typically need to season for 6 months unless you get lucky and find a portfolio lender or if you decide to go commerical.

There are a lot of different ways to make that happen and that typically boils down to what you are most comfortable with and feel like is most effective for you.

I know a bank typically asks you if the property has been rented for more than two years to treat it as an investment.

Typically, with a chunk payment of $10,000 or more on a loan, a bank will re-amortize your payments based on the # of months you have left to pay, and let you keep the same interest rate!

(Sounds like he did not adhere to that - this may be his only fault in this case.)Did the original contract state that any changes/extensions/etc would need to be in writing?

Those are the typical things you're always going to end up doing if you want to thrive in this business.  

@Jane Smith70%-75% LTV is pretty typical for an investment property refinanceHow much equity do you have?

My goal is to be able to buy single as well as multifamily homes and live off of the rent (long term goal) Ive also met with a broker who works with short sales, he takes on about 10 "projects" a year presents you with the short sales in area of interests (mainly Long Island) along with high and low comps, he asks for a percentage (unknown, at our discretion it appears) of the  profit after the property is sold, he typically works with investors who buy and flip. 

Reason I ask is typically you can't get LLC treatment if a property is financed.