Im looking at house hacking in Poughkeepsie and trying to cash flow or break even. I would be commuting about 1 hour 30 minutes to work in the city. Does have any tips for house hacking in Poughkeepsie?

The region/city/town specific information on house hacking is not nearly as important as the basics. Start with this book, it will get you to the point where you can purchase that first property.

House Hacking Book