Well those are suburbs of NYC, Middletown is Orange County, I'm from Brooklyn so I consider that upstate already, Poughkeepsie is in another county also out of the city and so is Newburgh. I guess if you have a job and don't mind traveling down to the city, I'm thinking an hour travel, maybe more from Middletown. I had a house upstate in Sullivan county which is the next county up from Orange (middletown). I think your going far and jobs aren't that great up there. Like I said unless you have one already. They are all beautiful areas.