Do you plan on renting out your current house or house hacking it? 

I started off with 3 houses on a lot and another house two lots down.

I know a friend who is an attorney, although they don’t specialize in housing law.

You mentioned student housing - What schools are they near? 

It's running a business NOT renting a house.  

Most old houses it is about 4 ft at the perimeter of the room, maybe less. 

Can you buy a house and be within reason of what your current rent? 

I bought my first house 2 years ago for 255k 20% down at 6.375% APR.

Purchase price: $120,000 Cash invested: $150,000 Dilapidated house.

I always am amazed when someone selling a $600,000 house brings me a listing agreement where they agreed to pay a stranger $30,000 to list their house for sale and they didn't even read the agreement much less spend the $250 to have a lawyer tell them that yes, if they sell it to their cousin during the listing period they still have to pay the $30k.