Hi there!
I currently live on the West Side of Manchester and can say it is a very nice city. The jail that is here is only a county jail, so you’re not going to see life sentence prisoners there.
Sorry I cannot give you opinions on schools, no kids. As for the North side of town, very nice area, just make sure you look at the properties any realtor wants to show you. When I was house shopping my opinion of what North side was seemed VERY different of what I was shown.
I’d say the ‘expensive’ north side would be anywhere north of Webster St.
Also, don’t be afraid to make a under bid on any house, a friend recently purchased a home and made a low bid and it was accepted! Surprising, but the market here is coming down some and you may find folks willing to deal a little. ‘
GOOD LUCK!