With regard to Chinley, the 07:03 EMT to Liverpool Lime Street regularly has 30-40 passengers boarding; The 07:57 Northern and 08:03 EMT services towards Manchester have a similar number again between them, with passengers gambling on which one will reach Piccadilly first if the Northern one is delayed at all. There is at least one regular passenger from out of the Hope Valley who uses Chinley to transfer from Northern to EMT with these two trains.
As far as ticketless travel goes, if one uses the 07:57, its important to sit as close as possible to the door where the guard does station duties when boarding to ensure you can buy a ticket from the guard. After New Mills Central, it is virtually impossible for the guard to get through the train to sell tickets, as it will be too crowded.
For the evening return, using either the 16:43 or 17:43 EMT trains (ex Picc times), these are often delayed between Castlefield Jct and Piccadilly; so again Chinley passengers take a gamble between these services and the Northern ones at 16:50 and 17:50. The gamble is usually on whether the New Mills South Junction signalman will hold the stopper to allow the express up the Hope Valley first.