House Hack in Expensive Market or Invest Out of State?

[Sean Dillon]

I live in an expensive market (Long Island), where breaking even or cash flowing on a property isn’t really possible right away. I’m 18 and currently living at home with low expenses.

My dilemma: Should I buy a duplex as a house hack and cover the negative cash flow to start building equity? Or should I take advantage of my low living costs and focus on investing out of state in a more affordable market?

My other concern is that home prices on Long Island appreciate quickly. Since it's already an expensive area, I worry that waiting too long could make it even harder to afford a home when I eventually want to move out of my parents’ house.

Looking for advice from experienced investors—what would you do in my situation?