I recommend doing research but don't spend forever researching.

I've flipped houses in areas I wouldn't want to live in and I've flipped houses in neighborhoods I can't afford (well don't want to spend that much anyway) to live in.  

Also, by keeping my GPA up, I can go to a university and only spend around $15,000.

I'm hoping to network and find resources on that end of the market, so I can add value to what he is doing.I'm sure I will find new things as I spend more time on here :) 

In rougher areas you might end up spending a bit more than 50% where the houses might cost less.

I myself would love to spend every morning walking the beach in La Jolla but I sure as heck can't afford any property there now. 

In the end, this means you are not actually "spending " you money...you are "using" your money, as many times as you want/can.Second, the success of this strategy as @Brent Coombs has touched on, is very much Market based (as in dependant on the RE Market you are investing in) since it involves getting properties at a discount.Third, it works best when you are using all cash, or a cash-like substance.  

I mean, if you dig and soils on the level of the floor will support itself, then the caissons are much more smaller (if not totally out of the picture) because it needs to carry less load, but that means you will need to spend for the basement -- is it a selling price increase?

Let your son spend the money, time, effort and resources to hire superior legal counsel and negotiate an acceptable solution.

Yes, we want buyer with high equity and in a good neighborhood, but you might want to add some criteria like:1. where the house is at least 20 years old, because that's when they feel frustrated and want to move out or spend money for repairs2.