First Time House Hack Oahu - Need Advice

[Braedon Page]

Two questions - 1) What are my best loan options to house hack in an expensive market without W-2 income, and

2) How can I best approach my first house hack to set me up to buy more properties in the future?

 I'm trying to do my first house hack on the north shore of Oahu. I've looked quite a few properties and while the other posts I've read in the forum have been right about it being a hard market to cash flow in (especially with the strict AriBNB laws), I've found some that the numbers work on in this area. 

I have up to a 50k budget to put down on the property, although I'd probably like to go as low as possible - an FHA loan for 3.5% down sounds great.

I don't care much about the size, beachfront or not, etc. I'm just coming out of college myself so I don't have crazy high standards, but I don't think I wan't to tackle a major fixer-upper as my first property. 

I have decent income, but I get paid as a private contractor which definitely complicates things.

I've found multiple properties that would cash flow fine - covering principle, interest, taxes, maintenance, etc. but I'm trying to figure out the best type of loan to take out as I don't have W-2 income.

I also realize that with the price of real estate in HI I will have an atrocious debt-to-income ratio after that first house and I won't have enough equity built up in the first year or two to access - any tips for how to go about my first house hack that will allow me to purchase more real estate in the near future? I've heard the guys talk about "house hacking a new house every year" on the podcast but I have no idea how that would be possible with the debt-to-income ratio I'd have. Thanks for the help!