I have been spending considerable time researching both those counties.
Here's how I would break it down:
1) You have family in Ulster, but depending on where they are in Ulster & where you would be in Greene, the distance probably wouldn't be much of a factor; unless it's north Ulster & south Greene. I have found both Greene & Ulster counties to have some breathtaking spots. I purposely allot myself extra time when I have business down that way. I love taking the side roads!
2) I've also found bargains in both counties. Although I am primarily looking at commercial property, I see a lot of residential when it's listed as multi-zoned. I have seen more available properties in Greene that depend on a well or other private water supply; vs. Ulster where in addition to Kingston, many of the smaller communities still have public water & sewer. So if that is a factor for you, I'd pick Ulster. But lots of folks do great with a well - it's all what you're willing to contend with.
3) The outdoor activities & recreation are, IMO, abundant in both counties & thru out the Hudson Valley. I cover a lot of ground in the HV; I would never get bored if I lived there!
4) Generally I think the commute to Albany would be shorter from Greene County, but only if you are close to a major route like 9W or 23, say. If you find a spot tucked way back, those country roads can take a lot of time to navigate in nasty weather. Vs., say, about an hour from the Kingston tolls to the Albany exit 24 tolls all on I-87.
5) The local shopping/downtown main street vibe/investment potential is why I would pick Ulster over Greene. Greenville is pretty much the "main hub" of Greene county. It's adorable, cute, and over in a flash. You can get just about everything you need; you just won't have much to choose from. Whereas with Ulster county, in addition to all the cool smaller communities like Saugerties, Rosendale, Hurley, etc., you have Kingston.
I think Kingston is going to have a serious comeback story to tell. It might take some time, but I do believe it's got the potential. You have Uptown, Downtown, & Midtown business districts; you have the Stockade, the riverfront, the Marina. Lots of cool shopping along Front & Wall Streets, a couple of larger shopping areas on 9W, a great live music scene & some of the most incredible dining in the country!
Good luck in your quest!
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