The Glossop/Cut Gate route looks to have some nasty bits of road and I did cut gate out and back a few weeks ago, so probs not that one, unless there’s anything special about the bits I don’t know (in and out of Glossop)
Doctor’s Gate recently had the bottom end, erm, sanitised – but in a positive way – to make the super boggy section towards the bottom less horrific. I rode it with a mate a few weeks back and it’s okay in a techy, nadgery way, but there’s not much flow to it and a couple of small sections are pretty much impossible for most normal human beings. Some folk love it, I’m not too fussed and the only legit access is via the A57 either from Glossop or the Ladybower end, neither of which are very pleasant, particularly on a mountain bike.
We got there using slabbed footpath on a quiet weekday, which is a whole lot more pleasant, but I still wouldn’t particularly bother again. It’s a pretty place to be though, so epic views and a bit of interesting exposure too.
Of those, I’d probably do a classic Roych/Jacob’s loop then extend on the Heyfield side over the Shooting Cabin / Middle Moor, but avoiding the road climb at the end on the permissive footpath that runs parallel to the road, onto Monks Road then some variant of the PBW – coffee at the Sett Valley cafe – then something over Chinley Churn before dropping back down. Either way round has pros and cons ime, I do both, but if you do it so you go down Jacob’s, do yourself a favour and choose to do the climb up on the Hayfield side on the bridleway that starts above Kinder Reservoir rather than the main track, and consider continuing on the fp that runs parallel and is an obvious continuation.