Your reporter from St. Louis was probably being intentionally negative regarding the food scene in Boston. Boston/New England has a great food scene. Not even sure what that salted caramel malt thing might be that you are referring to. The region is best known for it's seafood. New Englanders consumer more ice cream per capita than any other region of the USA, as a result there are lots of mom and pop home made ice cream stands all over, mostly only open during the summer months. Ice Cream is my favorite part of the New England summer. Your reporter should have made the trek to Kimball Farms.
One of the major industries in eastern MA is higher education. Lot's of universities in the area = lots of intelligent young adults. I'm not in the dating scene, being old and married for many years, but I can imagine the dating scene for a 20 something is pretty good. Those intelligent young adults also start lots of companies, making for a diverse and thriving jobs market. This jobs market is what makes Boston a desirable place to live and drives up the cost of housing. Housing in Boston proper is very expensive. Boston usually ends up in the top 5 most expensive places to live according to the people who study that stuff. The list of top 5s is usually along the lines of New York, San Francisco, LA, Boston, Washington DC. It wouldn't hold that spot year or over year if it wasn't a highly desirable place to live.
Trust me, the winters are horrid. The spring, summer and especially the fall are fantastic, to make up for the suck that is winter in New England.
Lived in the Boston metro area for 30+ years.