You really must read this blog by Richard Howe, Jr. daily, if you are interested in MA:05. It will give you insight on the Democratic side.
Richard Howe, Jr. is a good guy, even for a Democrat ;). He ran and won a normally hack position as Registrar of Deed for North Middlesex and turned his Registry into a statewide if not national model.
I wouldn’t vote for him for a position where his politics matters, but for something like Secretary of State which is more of an administrative post, I’d probably do so.