Also, should it be a separate LLC for each house?

Very different answers to your question depending on the answer to this one.If for a career path, I would agree with @Michael K Gallagher and find a brokerage that is actively doing deals, has a property management division in house, and has brokers covering each of the key market segments - multi-family, retail, office, industrial and land.

House in both are very safe.

Are you both on the loan and title for the house? 

Bought this single family home with the purpose of house hacking.

When I will be renting a room or basement in my house (that I will be buying as primary residence), I’m planning for the roommate to just zell me the monthly rent directly to my back account.

i'm would appreciate the communities perspective and input on the following question below.Property Criteria; House hacking duplex or triplex Purchase price: 260k - 310kEquity or Cashflow deal ?

With simpler management, you’d have less risk and steady cash flow.

Hi All,My wife and I just purchased a larger house on our block, and plan to keep our current home as a rental.

Once we got possession of the house we literally had to wear respirators to be able to enter the house the cat urine smell was so strong.