Richard, if you happen to have a copy of a New Haven Railroad Time Table (any year), your attention is invited to Rule 1612, which is a little bit on the lengthy side (ten paragraphs taking up an entire column of the two-column page). This rule covers who, where, when concerning putting up or putting down the third rail shoes.
Concerning a rake-off block at Wilton, this could well be a post-New Haven installation. With Metro North equipment and operations, and high-level platforms everywhere, the need to ensure shoes were up may have changed.
Concerning communicating with the train's head end, back before the days of radio, the conductor communicated via a signal cord located in the vestibule. A yank on the cord would activate a whistle in the engine's cab. In return, the engineer would communicate with the conductor via the train's whistle. Communicating signals are covered by Rule 16 in the Book of Rules, and engine whistle signals by Rule 14. You'll note that passenger equipment of that time had an air hose, a steam line and a signal hose. The signal hose allowed the rear end to communicate with the front end pneumatically.
As for anyone getting raked over the coals concerning shoes up or shoes down, one must remember that these were pneumo-mechanical devices, prone to occasional failure. Now, while totally ignoring the requirement to raise or lower the shoes as appropriate might warrant further action, a simple malfunction was usually dealt with in accordance with Rule 1612.
On a more personal note, although I spent a few years with the New Haven (and Penn Central) as an S.S. Operator, no train service at all, most of my transportation career was with the U.S. Army, starting off with traffic management and ending up as a Logistician on General Staff. My schooling and experience involved me with rail, truck, aircraft and oceangoing transport. It was incumbent of me to become familiar (not an expert) with anything and everything involved with the movement of people and things from Point A to Point B. Pick up and load an M-113 armored personnel carrier onto a flatcar using two 5-ton wreckers? Been there, done that, but I wouldn't recommend it. Train troops how to load tracked and wheeled engineering equipment onto flatcars, including teaching them how to properly tie them down according to A.A.R. rules? Been there, done that. Get shot at? Yeah, that too. Been out on the open ocean on a 100-foot Army tugboat and have been underground in the Nevada desert with a unit supporting the DOD Underground Nuclear Weapons Effects Testing Program (and when shipping classified radioactive material (Radioactive Yellow III), the first three pages of the shipping documents, which I had to create, were warnings - the fourth page was the actual description of what was being shipped).