Is it built to 'living space standards' and up to new IRC codes?

Not sure how to navigate buying one specifically to live in. 

Rented my house we originally lived in 12 years ago because we couldn’t sell it when we moved and that’s how we got started. 5 years ago we made a plan and an effort to accumulate multi family properties and did that.

I am interested in having these conversations and learning more.

Being based in the Raleigh area and having lived in Chicago I am biased toward Raleigh area for investing. 

was always a fun conversation from those days (note that this is only lawful if you are actually licensed and formally affiliate that license with the firm you work at, which requires approval from your employer).And then I noticed several REI pick-me-up deals (a 'pick me up' deal is where a big bank can't figure it out, and it falls in your lap two weeks into escrow, with two weeks until scheduled close of escrow) where I figured it out when my LO couldn't and/or without his input.

Since you're living in it, the worst case scenario is paying the full mortgage which hopefully you would be able to do anyway. 

However, you can use a cost segregation study to break the property into different class lives and claim more depreciation up front.

I would go with your gut on which home you would rather live in.

I originally lived in the casita while I rented the front home out.