Wyhog, the yard in Sheridan looks pretty flat to me, at least near downtown, but I guess that can be deceiving.
Yes it can be deceiving. When I first moved here in 1975 I thought the railroad was flat from Ranchester to Parkman, until I went up it on a train the first time. Five units on the point, two manned helpers shoving on the rear, and we were going all of about 11 mph. The whole earth surface in that area is tilted so at first glance it doesn't look like much of a grade. Moral, you can't tell a railroad grade just by looking.
Click on the first photo on the page below (not the MRL banner pic at top). This train is climbing the 1.6% grade eastbound at Sheridan. If this train is only one mile long (5280 feet) its rear end is 85 FEET LOWER than its locos, and its rear end is still coming out of the yard. That is not flat. The locos of this train are approximately at the same spot where the coal train broke in two that I typed about in my post above.
Sheridan Hill
Cars, locos, and trains will easily roll west out of Sheridan Yard itself (and roundhouse tracks) if not tied down. Look at the 5th, 6th, 7th photos on the page below. That is what happens in Sheridan Yard if a loco loses its air brakes in the roundhouse area and its hand brake is not set. The SD60M has rolled about 1/4th mile before it hit the derail. And this was in sub-zero weather with very stiff bearings and gears.
Yard rollout
Hand brakes and air.
If a car has its air brake set (especially if set in emergency) and you then set the hand brake all you are doing is taking the slack out of the chain until the very last turn, which is harder. Hotwater is of course correct, the length of chain you have to wind up is the same whether or not the air brake is set. It is just easier and thus faster if the air brake is set because the air brake piston already has the brake rigging moved and taught and the brake shoes pressed hard up against the car wheels. Basically then all you are doing when winding the hand brake is taking up chain slack and at the end setting the hand brake ratchet pall. Now if the air brake cylinder pressure leaks off, the tension force that the brake piston was holding is now applied to the hand brake ratchet pall. That makes it very hard or impossible to release the hand brake. So sometimes it is necessary to charge the car's brake system then apply the air brake (possibly in emergency) to re-transfer the tension force of the rigging and shoes from the hand brake pall to the piston. Now with most of the force off the hand brake pall you are able to release the hand brake. Been there, done that, countless times.