That's one hell of a long day out!
I'd go up South Head, Mount Famine, Roych, Rushup Edge, Mam Nick, Hollins Cross, down to Edale, UP Jacobs, down Coldwell then fork R onto Broad Clough, it eventually drops you down to Kinder Res. From there if you're late/knackered you can get back to Hayfield, if not then up the cobbled climb, Shooting Cabins, Middle Moor, Little Hayfield, up to Blackshaw Farm then down whichever way you want to the Sett Valley Trail. By this point you're just circling Hayfield so it makes it an easy bail-out cos what you've described is proper tough.
If you get down to Sett Valley Trail and are still feeling good then up the quarry road, New Allotments, Chinley Churn, Far Phoside to finish.
Doing the big Hayfield loop first means you're back near Hayfield by the end of the day and can add on bits round Lantern Pike, Chinley Churn etc as time/fatigue dictates; if you try doing that to start then end up half way round the Hayfield loop in Edale when you're blown or it's getting dark, you've got a hell of a trek back.
Jacobs up is a slog and (for mere mortals) only partly rideable but the rest of the loop is MUCH better done that way round, you get several options of cracking descents off Mam Nick, Rushup Edge is better heading from Roych down to Mam Nick and the rest of the route round there is just wide gravel tracks anyway.
