Went to college (A-levels) in Marple, grew up in Stockport - Glossop's OK I think, not sure about schools, although a lot of the kids from Glossop used to come to do their A-levels in Marple (I don't think the 6th form provision over there was too good) Hattersley was and is rough, Stalybridge (Staly-vegas) not much better, Gee Cross / Hyde are all a bit rough in places. I think the closer to the peak district you are, the better. Marple and Mellor are quite nice, and there are reasonably good schools / connections by train to Manchester / shopping, etc from that side of the hill. Had a friend who lived in Tintwistle which was fairly good. Nice walks around the reservoirs, hills, etc.
I believe there's a certain Viscount of Derbyshire who posts on these boards quite regularly who knows the Chapel / New Mills side of town fairly well. Chapel en le Frith also has the direct trains to Manchester if required (although the station is nearer the railway than the town) - driving to Manchester from Chapel via the A6 is not a pleasant experience on 2 or 4 wheels. New Mills has the benefit of TWO stations - both of which are very small, Hazel Grove has good(ish) trains- more frequent than New Mills. Glossop is also on the train line, and has slightly nicer electric trains if I recall correctly - because it was linked to the main Manchester - Sheffield line before the Woodhead fire which closed the line.
Personally I'd be inclined to live somewhere which gives you the option of a train or tram into the city centre, because driving can be a nightmare: like any big city, the roads are very congested, with the A6 probably among the worst of all. That said, Glossop might be better for bike commuting, as the A57 route through Gorton, etc is a fairly wide road, so filtering shouldn't be too bad.
My Dad was a teacher in Duckinfield (hard work I think!), then various primary schools in and around Stockport over a period of around 30 years - also seemed to be hard work, but he retired a few years ago now. Some nice-ish primary schools around those parts, particularly in the more south / south-central Manchester / Stockport areas - depends what you want though.
Hope that's of some interest / help! Feel free to reply / PM / email me if you want any more info.
Stuart.
EDIT - I've just thought - the friend I had in Tintwistle was a property developer (or the daughter of a property developer) - and she's now helping to run the family business - they used to quite often have the odd empty house which had either just been renovated or was available for let - I'll drop her an email and see if they've got anything.