Without more information I think you need to do some more research on the fund, what their investing in, what type of debt/leverage their using, their timeframe, their different underwriting assumptions, etc.

The place seemed to generate at least $2K a month net after all debt and expenses consistently, and though the market seemed very small and unexciting, I was drawn to the promise of big cash flow.

Anyways he may not be a billionaire as it’s likely he hasn’t other investors or debt on these properties.  

First step....find a local Wxperienced short sale agent.....the bank will require it to be listed for a short time and more importantly someone who Knows what they’re doing needs to put it together, including determining what add’l money a buyer may need to kick in to junior debts Before making an offer. 

It eliminates the competition!

The more debt exists on a property from the owner/seller, the worse it is. 

The company has expressed a strong desire to want to hire me before or when my second contract expires.Pay: I make a little over 1K a week (after taxes) with very low reoccurring debt due to me currently living at parents house.Goal for purchasing house: Buy 4-5 Bedroom house.

Noah,If you're already know what your "issue" is then start by working on eliminating this "issue" of yours first and learn from the people that are close to you and have been around the REI business for a while!

And he can pay monthly debt up to 2k. 

Where operators get into trouble in larger MF is lavish assumptions going in, placing the wrong debt on the deal, and not stress testing the deal/market.