In the Houston area, which I assume is like most major areas, there are companies that just handle short sells.  

Figuring that the majority of agents quit within the first 6 Months to a year because they don't earn enough income you are in the perfect spot of not needing alot of income since you are still in school.

Five years ago I graduated from Virginia Tech with a major in Property Management and a minor in Real Estate.

So a 50k loan at 2 points makes them 1k in fee's  that's a ton of risk for such a small loan and if it turtles you can lose half your money in that market no sweat.. that is the other major hurdle. 

I am thinking we would use the equity to put 5% down on a slightly bigger family house for us (with a basement apartment), and then use the vast majority to put 20% down on a 4-plex in a less expensive town within an hour of us.

But to investors, it's become a major expense, and the frustrating thing is that it is an expense that purchases nothing, except to pad the pockets of an HOA.

What are the major things to watch out for?

It is revitalizing and close to bus stop, downtown and 2 major highways.

I am a business major at a local university in the Seattle area looking to break into the real estate industry as soon as I graduate in 2017.

But it is a major risk to have an assistant, because basically any error you make while assisting your sales person will be his responsibility.