My thoughts: if you have a steady job that can support the negative cash flow, and you don't plan on leaving Long Island for at least 5-7 years, I would house hack. 

We wasted several thousands of dollars with them until we realized that they weren't able to handle the project...After we fired them they turned around and offered me a job ;>) - I politely declined as I don't think the industry is setup to help us. 

The vast majority of contractors won't want to give bids on properties while under contract unless they have a relationship with that person from prior jobs.

In Columbus, you can still find the 1% rule and there's amazing appreciation potential due to how much population growth, job growth, and companies moving/developing there (recently Anduril just announced another 4,000 jobs coming to Columbus Ohio on top of Intel, Google, Amazon, FB, Nationwide, Ohio State University, etc.).

Are you looking to quite your W2 job--STR might get a leg up because of the STR loophole in becoming a real estate professional? 

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

Depending on how long it takes you to save up the amount, you might want to also allow for inflation on that amount for your continued savings.[2]   Read Rich Dad poor dad.[3]   Think about getting a second job - possibly a temporary job - save a 100% of the money.Just my 2 cents.

Just so you know, Vrbo and Airbnb will not allow you to receive an inquiry through their platforms, and then take the booking off-platform, they want their cut of the money. 

Huntsville, in particular, has strong job growth, steady appreciation, and a high demand for quality rental homes.

I have seen so much growth in Columbus when it comes to appreciation and job opportunities which I have experienced.