Sell my old house or keep and rent out - first house hack

I'm thinking about moving to a bigger house that has a bottom section I can rent out and house hack. Either a split level style or separate in law suite downstairs. 

Trying to decide if I should sell my old home or keep it and rent it out. 

Current home- worth about 270-300k

Owe-167k on a 15 yr fix @2.75, payments are 1160 a month, not including tax/insurance. 

Rents in my neighborhood go for 1600-1900

My target range for the bigger house would be a max of 330k and I think could rent the bottom out for 800-1000 per month.

Scenario 1: I rent out my old house, I factored in taxes,  insurance, 5% for vacancies and 5% for repairs and I'm estimating $150/month cash flow.

My payments on the new place would be about $1750 - 900 from the tenant = $850/ month. 

I would also need to come up with a down payment of around $11k, maybe borrowing from my 401k.

Scenario 2: I sell my old home, net approx $100k after commissions and then put down on the new house. Then my payment would only be around $1284 - 900 from the tenant = 384 month, practically living for free. I could then use that monthly savings to save up and start real estate investing, probably with a flip. 

The thought of carrying 2 mortgages is scary as I am brand new to all of this. 

Appreciate any feedback!