Now on to the first pic. The key thing here is the placement of the tail block in relation to the pole hinges. The pole hinges really need to be in front of the tail block. First off it's needed to allow lifting the poles with the winch as in second pic. Secondly if the tail block is to far forward and you lift a load with the poles near straight up you will pull the poles over onto your headache rack. If you look closely at the first pic you can see the original placement of the pole hinges by the original builder. He put them on the back corners of the bed. This didn't work well.
I like the pin through the pole setup the best since it's the least likely to come apart if a side load happens.
With all respect to you Irish, I will have to disagree with your statements, and your logic. I will explain my self as best I can.
1st off, the pole hinges do not "have to be in front of the tail block" - Never seen a set of poles like that - Never built a set of poles like that. Never ran a set of poles like that. Sorry.
2nd - That has squat to do with raising the poles into the working position. As long as the line coming off your winch drum is below the line coming off the pole cap and going over your roll, the poles are going to raise up - Period. The higher your poles are from horizontal, the easier they will raise up.
3rd - Gin Poles were NEVER designed to work at absolute Vertical - And I have NEVER seen, or used a set of poles in the air that wasn't secured in the working position with tie-back chains. When the pole cap is laid back just behind the roll, and tied back with 1/2" System 70 chains, you can damn near push with them. To operate poles with a load at Vertical, or without tie-back chains is sheer recklessness.
The last point - Not to knock a man who is doing the best he can with what he has, but that is NOT the "Best set up for a set of poles - A manufactured Pole Cap is - The hold back cables, chains, or winch line attach to the Pole Cap. Agreed poles are not really designed for side loading - But a properly buile pole cap that slides into the poles 12" or so, then pins into the poles, will not come out - Even if you drop the poles.
It is kind of hard to see from the photos but I will explain myself:
First Photo: The Snatch Block/Tail Block/Sheave (Whatever you want to call it) attaches to a steel bracket called the "Deadman" that drops below the deck surface when not in use. As you can see from the photo - The Pin holding the Snatch Block to the Deadman is in-line with the hinges on gin poles.
Second Photo: When the poles are in the air, and the winch line is tight, the Deadman leans towards the winch, and the Snatch Block and winch line are on the winch side of the gin poles - The opposite to what you described.
Please note as well the tabs on the poles, and the tie-back chains that hold them in the working position.