Especially after capex, vacancy, management fees, etc etc. 

You will have to pay higher personal income tax rate, versus waitingtill after one year for lower Capital gain tax rates.

@Brad Kanouse Using Traditional IRA funds for an investment property typically incurs income tax and a 10% penalty if you’re under 59½, as investment properties don’t qualify for tax exemptions.

This is also tax deductible.

So many variables can turn a deal sideways from 1 hour to the next - i.e. inspection findings, title issues, contracts, financing issues, taxes, dept. of buildings/local municipalities, etc.I'm glad to hear you made it through the challenges, and it sounds like you'll be able to leverage this experience as you grow your portfolio.All the best to you along your journey!

The property was rented and generated $160 cash flow after mortgage, taxes, insurance and property management fees were paid.

I know that i could buy my next multi family property as a primary residence close by move in, rent half live in the other and than rent where i am now which would cash flow upwards of 1k monthly, or i could buy another multi as strictly an investment property out of state which would be a lot cheaper (taxes and cost of property) and a lot more landlord friendly laws than New York, i guess i’m just undecided on which route i want to take and I’m trying to weigh the pros and cons of each scenario.

Working with the city to find a solution.There is a similar situation near me where an investor bought a short term rental house, rehabbed it, ran it for a while, and then got in trouble with the town after a neighbor complained and the town said short term rentals weren't allowed in the community. 

Whichever loan that you decide to use, the interest will be tax deductible due to interest tracing rules.

For example, what would the cash flow be like after you renovate and lease out at the new rates?