I'm open to other areas as well, but based on what my realtor friends say about where I live now makes we want to get my foot in the door here. 

I would not and I would not recommend anyone to touch this with a 10 foot pole. 

House hacking is how I personally got started with real estate investing and how I help the majority of my clients get their foot in the door.

That's assuming things are linear-- they are not.

I refresh our lots list every few weeks and look at infill lots by price per acre, density allowed, new build average price and price per square foot, deliveries per year, etc as a driver for it.

I know it depends on the number of seams, wall height, amount of doors, windows, etc. but on average, how much caulk would you guestimate a painter would need to paint a 2,000 square foot house?

C/D neighborhoods, although even C neighborhoods are now selling for over 150 square foot and still need rehab.2. 

It has 9 foot ceilings, some plaster of paris and need to adjust a vent.

It costs 10k for them to complete one deal for you and to get your foot in the door.

House hacking is a great way to get your foot into homeownership AND investments. two birds, one stone!