Much easier to do business there in terms of regulation but harder to come by a reliable cleaning/handyman/PMteam and smaller pool of contractors.You need to decide what is important to you.

Is cash flow the main objective?

High Maintenance Costs: Escalating maintenance costs can erode your profit margins.Change in Neighborhood Dynamics: Shifts in the neighborhood that negatively affect your property’s value are a red flag.Better Investment Opportunities: Selling might be wise if you've identified a more lucrative investment opportunity.Cash Flow Necessities: If you need liquidity, selling a property can provide a significant cash inflow.Tax Implications: Sometimes, selling can be advantageous for tax reasons, especially if you can benefit from capital gains tax laws.Personal Financial Changes: Changes in your personal financial situation may necessitate liquidating assets.Retirement Planning: Selling investment properties can be part of transitioning into retirement.Portfolio Diversification: Selling might be necessary to avoid overconcentration in real estate.Legal or Regulatory Changes: New laws or regulations can impact the attractiveness of holding onto a property.Ownership Challenges: If the burden of ownership outweighs the benefits, it may be time to sell.Real Estate Market Trends: Anticipating a downturn in the market can be a reason to sell early.Interest Rates: Rising interest rates can reduce the pool of potential buyers and lower property values.Property Value Appreciation: If your property has appreciated significantly, taking profits might be smart.Lifestyle Changes: Sometimes, personal life changes dictate a shift in investment strategies.ConclusionDeciding to sell an investment property is a complex decision influenced by market conditions, personal circumstances, and future investment goals.

This will be my first investment property and I know NY is not an investor-friendly state but the cash flow with this deal makes it worth it to take it down.  

On a cursory review, it appears that your cost of debt exceeds your capitalization rate, suggesting negative cash flow.

Plus, there's still so many positive cash flowing and 1% deals here in Columbus Ohio.

The option that I am entertaining is to purchase a multi-family that will cash flow enough so that altogether, the two properties cash flow positive.

A Cost Segregation study is an IRS approved federal income tax tool that increases near term cash flow by utilizing shorter recovery periods for depreciation to accelerate return on investment.

Just got home from 3 hours of clean up at a property today, in the cold and rain.

For instance, I make much more money in Appreciation (the Investment aspect of RE) than the fees I charge for managing the property or even the Cash Flow.2) "Cash Flow is NOT a characteristic of the Property.