FWIW - I beieve all artesian wells are "drilled."
When I was a small child we lived on a property serviced by a dug well. This property is now the "Wilson's Farm Stand" in Litchfield NH. It was owned by relatives until about 25 years ago. I still have links to that community and to the best of my knowledge that well has never gone dry and is well over 50 years old (pardon the pun!).
I'm sure there are many factors leading to the reliabiity of a dug well. Topographical details are probably most significant. If the well is closer to the top of a slope than the bottom it may be more prone to going dry, like when you stand a wet sponge on end there will be water at the bottom longer than the top.
As for the risk of contamination... The well I described had a stone wall replaced by a concrete ring, around 1965, to reduce surface contamination. I believe the incident that led to this 'improvement' was a skunk getting into the well house and drowning. Wells can also be "skirted with impervious materials so surface water is diverted further from the basin and filterred a little more by the surrounding sand or soil.
There are probably books available at the library that will provide you with some insight to decide if this is going to be something you'll want to work with. You probably wont want to pay someone to evaluate the well until you've signed some kind of contingent purchase agreement, then you could include a favorable inspection of the well as a condition to complete the sale. They will advise you of the practicality of improving or replacing the well.
If this location has made your 'short list' you can also go to the Town Hall and speak with the building inspector's department. They may have water quality information for various parts of town and informational pamphlets on this and other topics of interest to to you. While you are there, ask about a copy of the map that shows the propery lines in the neighborhood. I forget the technical term for that, if there is one.
Good luck!
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