I assume they collect a proration every month for property tax?

That one is a big deal for rebuilding.I've also heard of property tax reductions for properties significantly damaged during the storm.Depending on the property and what you want to do, the hurricanes affected property tax, insurance, and permitting in a lot of ways.

To transition to multi-family properties, research landlord-friendly states like Texas, Florida, Tennessee, and Indiana with favorable eviction laws, lower taxes, and higher rental demand.

Bonus - the interest on the loan is tax deductible!

Your New York LLC is considered a "foreign" LLC to Pennsylvania.

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

We have sold (tax free), kept as long term and/or short term rentals as well.

Assuming property taxes + insurance added don't go above $1,100 total, you could maybe make this work. 

3) Your $250k with 30% down => about $750k (you also need funds for closing costs, taxes, etc.)

I think there are some tax benefits that outway the small negative cash flow that you're currently experiencing.