Instead of jumping into an expensive Long Island market with negative cash flow, consider investing in a Texas market like San Antonio, Houston, or DFW suburbs—these areas offer strong rental demand, lower property taxes than NY, and better cash flow potential.

When including maintenance/cap ex, vacancy, pm, misc he will have little, and possibly negative, cash flow.if he invested almost $250k to add less than $150k of value (assume some of the current value came from the home appreciation), there is no cash flow until the initial negative equity position is recovered.  

In some cases, after running the numbers, I’ve even faced potential negative returns, causing me to miss out on promising deals here in South Florida.That brings me to my question: I currently own two homes—one is my primary residence, and the other is a rental property.

My question is - is it foolish to hang on to this property that's at a negative cashflow, or am I on the right track thinking of the longer term benefits?

Is $150 negative cashflow a lot for you?

Perhaps it's a negative reflection on the fact that fame and celebrity often in this country give individuals free reign to commit crimes with out penalty of consequence. 

This creates a large negative equity position.  

I have cash flowed negative almost every month.

Isn't that negative or neutral leverage at best? 

I'm making two assumptions here - it will take you a year to get the tenants out, and so you are cash flow negative for a year, and that year of negative cash flow is a lot less than the loss in sale price you will need to take to get it sold as-is.