I wish I could help more and give some great insight.
I can say this - we would never move to Worcester at this point in our lives. It is a challenged community school-wise and crime-wise. I lived there when I was in my early 20's due to my job. It is a tough city. Not a place that I would live again unless I were retired and found a pocket of the old, gorgeous Victorian homes. It is a blue-collar, working class, factory city (which I can say proudly because I am from one, too, but my town was teeny and this is a city). But, standard for New England, the factories have moved out. I know plenty of folks that live all around Worcester but none in Worcester, itself. They are talking about extending the commuter rail line into Worcester from Boston. If that happens, it will gentrify rapidly. But that's way down the road. Having said all of this, I know there are gorgeous pockets of Worcester with hard working people. I think if you have a child you would really, really have to find a niche program in the schools or private school/parochial school them. Some great colleges are there - Clark University, Holy Cross, and WPI (a phenomenal sciences and engineering school).
Gloucester - north shore. Generally tend to have decent schools. Gloucester, I believe, lags behind a little bit. It is a fishing community - great location - awesome location. But, again, to my knowledge, lags behind a bit. There is tremendous wealth on the north shore and there are many high performing school systems - Hamilton-Wenham, Newburyport, etc. Gloucester is middle of the pack, I think. If I remember correctly there was a big scandal when I first moved back here - maybe 6-7 years ago. Maybe it was the whole trying for a baby thing by the teenagers that made-for-tv movies replicated. Was that Gloucester? I can't remember now. Again, hard working community.