After many years of looking for a home in the Berkshires and exploring many of the towns, we finally decided on and recently built a house in Lee. It's a great town for many reasons (in no particular order)...

• Pretty affordable real estate compared to the more expensive towns of Lenox, Stockbridge and Great Barrington that surround it. You have affordable very rural options and in-town options (easy walking to downtown).
• Lower real estate taxes than these same three towns mentioned above.
• Unlike Lenox and Stockbridge, which have a lot of out-of-state people who own 2nd vacation homes, Lee is more of a local and very charming community where so many great people know and look out for each other. (Although we believe Lee to be a sleeper town that you'll see many out-of-state people investing in over the coming years, since real estate is scarce.)
• Quick access to the MA pike, which makes it easy to get across MA and also to many other places in states like NY, CT, VT. This is also important if you need to have access to airports (Albany and Hartford).
• I hear the schools are pretty good (our own children are grown so no info to offer from personal experience on this).
• It has solid tourism, which supports a great downtown that is composed of many wonderful shops and restaurants, some of which tend to stay open far later than those in surrounding towns mentioned above.
• Lots of outdoor activities access with October Mountain, Laurel Lake (which has a town beach), and many trails. Quick access to Butternut Skiing and numerous others.
• Lots of shopping options. Lee Premium Outlets are in town and offer access to lots of very affordable shopping. Access to the MA pike makes it easy to get to shopping in places like Springfield & Albany. Rt. 7 corridor makes it easy to get to places like Pittsfield and Great Barrington for shopping.
• Excellent police and fire departments.
• Strong "community" with multiple churches, charities, town parades on holidays, etc.
• Lee is being built-up with significant investments. Eagle Mill (on the north side of the downtown area) is being rebuilt with a commitment of roughly $60M.
• Surrounded by solid hospitals in Pittsfield and Great Barrington that are quick to get to, with lots of access to medical services in the area.

I'm sure you'll evaluate all info provided for all towns. Good luck in your search.