Hi Megan,
The wife and I looked very seriously at Saugerties for a long time.
First the positives: Saugerties is geographically beautiful, and has a great downtown.
It is a little depressed in spots, and like much of New York, the properties tend to be quite a bit overpriced compared to rents, and once you factor in property taxes and other costs.
It could probably make a very nice place to live, and we almost pulled the trigger on a place there before deciding to move to New Hampshire instead.
So why didn't we buy in Saugerties? Because, in our experience, very few homes we might have been comfortable owning in that area currently make any sense from an investment standpoint.
You're just not likely going to be able to buy a place there right now and have it cashflow as a rental property or BRRR, or have it pencil out anywhere near being a profitable 70% ARV flip.
In our experience, the rents just aren't high enough, and the home prices just aren't low enough—even when they need a lot of work.
Some eventually sell for far below their ask and may be an OK deal then if you're savvy enough to make that happen. I recall one property that was originally priced at $150-$170k, and we penciled it out as being worth about $50k-$70k for a modest return.
It stayed on the market for more than a year before it eventually did sell for closer to the $50-$70k range to someone brave enough to wait and wait and then bid super low. So there is always a chance of finding something.
That said, there may be exceptions, and things may have changed from a couple years ago. But we ran the numbers on about a hundred places and came up pretty empty compared to where we wound up in New Hampshire, where properties penciled out much better.
(I have come to think that New Yorkers are a little delusional about their property values. As a life long New Yorker till now, I get to say that :)
That said, Saugerties is a lot better on all these fronts than say, Westchester, or some of the even more developed upper Hudson valley towns where home prices are completely divorced from rents, and only speculation (or habitation for your own personal enjoyment) is possible as a strategy.
If you're talking about investing, rather than speculating however, the game around that general region seems to be buying rental units in C or D properties in C or D neighborhoods and finding renters who can pay modest rates based on welfare payments.
That's not something we wanted to get involved in personally. Even then, I'm not sure the cashflow is tremendous in the region, though there are probably exceptions and some people probably do quite well.
Well, that's quite a bit of typing. But I hope that helps! Your experience may differ. And your luck as a speculator may be different than for a pragmatic math-loving investor. Good luck! Please let us know how it turns out.