Advice on House Hacking in NYC ?

[Angelica Rose]

Main Questions: What does it mean to "breakeven" when renting out a room in your property? Is it worth it to invest in your own property in an expensive city like NYC? Or do you think one should focus on "real investing"? Is investing out of state a wise decision for someone only making 50K (before taxes) in an expensive city ? 

Is it possible to actually have your roommate paying most of your mortgage in an expensive city like NYC, via house hacking?

Background:

I'm in the process of saving up so that I could possibly get some property in NYC in about 2 years. I've heard a lot of people talking about House Hacking. This seems like a win-win to securing property in NYC, given costs of rent are likely to increase and there's some sense of security. (Although, condos and coops often have maintenance fees). I've also considered investing in property outside of NYC, but it's more intimidating and I'm not even sure I should be one doing that, as I'm relatively young (28), not wealthy at all, not married, and am just beginning to build up my savings.  The downside is that I give up the freedom to live in whatever neighborhood I want to - I could only afford a handful of neighborhoods further out in the boroughs. I dont mind the longer commute and I suppose I could always rent both rooms in the property out and start renting again. 

Sorry for all the thoughts/questions. I'm trying to work through what my plan will be. Thanks!