House Hacking (FHA) in NYC or OOS investing w. turnkey companies

[Alejandro Obando]

New Investor, trying to figure out what strategy I could utilize for my very first investment. My goal is to invest in a property that will generate roughly $300/ month in cash flow within the first year. currently saving capital for when I do make the first purchase, I am about 5K away from hitting the 3.5% down on an FHA property in NYC, Since I live in a very expensive market (NYC) it is challenging finding a property that will generate any cash flow at all.

I've been researching, reading and networking for the past 6 months 

Using sites such as "Redfin, Zillow, Trulia, Craigslist, Etc. to find properties and using the BP calculator to analyze properties, 

(goal is to analyze 100 properties by the end of the first quarter in order to truly understand how to analyze properties and cashflow).

I have no experience with OOS investing but I do see the much lower entry point with investing OOS. still not sure whether OOS investing is the right strategy since I will be relying on other people's actions/ commitment to managing the property.   

Any insight on other markets to look into or other strategies to use will be greatly appreciated. 

Thank You 

Alejandro Obando