Not house hacking is my biggest real estate investing regret.

I would keep the rentals there after you leave as 1031 exchanges must be done exactly right, one little mistake and you will owe a bunch of taxes. 

You can hire someone who lacks experience and can be trained, which may cost less but can lead to more mistakes along the way.

My 2 biggest pieces of advice... 1) If you want the fast track, get a mentor - but the RIGHT one...it's a crowded space and we definitely made a mistake selecting the wrong one the first time around (now we're with an amazing group and have closed over 400 doors in 2 years). 2) Don't fall into the trap of thinking you have to start small ...you don't. 

With this scenario I think one of the biggest decision factors is, are you eligible for a sec 121 exclusion? 

As you and Joe have mentioned I do believe that I made the mistake of thinking that the county site showed the FMV when in was only the assessment value for tax purposes.

We are on Long Island, NY and prices are pretty high but I'm wondering if there are any options for me to make this into a positive as my first rental property or if this would be a big mistake.

Now go do more and don't repeat previous mistakes.

@Matthew RiberaThe biggest gift you will give your children is their ability to achieve on their own.

The deals are out there, but I think the biggest key for me transitioning to MFH was lining up a reliable lender.