I'm born and raised in Hawaii with no formal education other than a High School diploma.

Area schools show "average". 

I graduated school with 30k+ of student debt which I have paid off in less than 3 years.

My little kids went to school in Drain.

As of yesterday it was brought to our attention that condos in a worse school district (we are either number one or number two in terms of best school district) that is a mere 5 min away, has listed at $250,000 for 1,631 sqft or $309,000 for 2,500 sqft.

My girlfriend is doing her clinicals there for med school, so I'd like to buy a house there for the next 18 months, then rent it out.

His advice was 1) probably don't invest for another 2 or 3 years because it is a sellers' market right now 2) do not get a real estate license yet because yearly fees are expensive, but that I should get one in 2 or 3 years when I start investing 3) learn my markets (Austin and back home in McAllen Tx) by making a spreadsheet of property listings and info about them and 4) focus on school to get a high paying job in a few years to help pay for my investments in real estate. 

The top submarkets typically have the lowest crime and highest school ratings.

Or do you somehow factor in condition of nearby properties, distance to schools and shopping, nearby parks, area crime, rating of nearby schools? 

Lots to consider,, I guess the location to your school is primary and if it's to far away it's going to have a large impact on what you maybe able to oversee.Money wise I'd probably suggest a LLC for the 2 of you..