I'm probably in a little bit of a different position; but here's my perspective as a 29 year old who's in the process of deciding where to buy our first house. Because we talk about some of these same issues.
We both have family here, yet how do you balance being close to family and friends versus the cost and style of living? To me that's really at the heart of any decision to move. That, and how your job fits into the picture, but it sounds like that's not an issue for your family thankfully.
It's hard to do, but can you put a price on what being close to family and friends is worth to you? Because for me at least, I look at homes on LI, or in NJ, and I see the same house in a similar neighborhood in Charlotte or even Maryland and they're selling for $150k less. And the property taxes are just slightly more than half of what I would pay here in the metro area.
So, while it's never all about money, to some degree you need to be able to compare apples to apples, no? Do I want to live near my family (and hers), in a smaller home, and enjoy the NY I grew up in? Or, do I want, for example, 1000 more sq feet, in a newer home, but out-of-state ?
I haven't found an answer yet. So if you do, let me know. But I think anybody comparing two places to live has to find a way to put a value on something that's not naturally quantitative. Not sure if that helps, but that's what I've been mulling over lately myself.
Good luck with your decision.