(So therefore we wouldn’t have to pass on the cost of the repair to him ie. the tenant).Now, several months later, I contacted the contractor to ask if he would be to provide a price estimate for a different job at our house.

I've found that Louisville offers some nice pockets.  

Huntsville is a fantastic market with strong job growth, a booming tech industry, and steady rental demand.

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. 

That 2nd requirement is  what makes it close to basically impossible with a W2 job.

With my W 2 job I might not be able to fly to these areas and vet them.

I think a better option is to get a job in property management.

Hello BP community,It's nice to see so many discussions from like minded people!

My goal is to buy one rental per year with price between 150k-250k for the next ten years (if i get to keep my job). 

Use your W-2 income to qualify for multiple loans now, stack a few properties before quitting your job, and consider BRRRR or DSCR loans later to scale.