Last time I was using a 40' extension ladder, it was a major challenge to retract it back from being extended and up against a wall. There were two of us and it was seriously scary. Could have gone wrong and crashed, doing damage or worse to nearby building, vehicles and us, due to it size and particularly weight.
Is there a way to do this securely or is it always, for the lack of a better term, a crapshoot?
Your ladder should have a rope and pulley mechanism for extension and retraction. Make sure you understand how it operates to prevent finger injury. Normally it's simply a matter of pulling down on the front rope to raise the ladder. To retract, lift the ladder a few inches using the rope, which allows the retention brackets to release, and lower the ladder extension with the rope.
Walking the bottom out to lay the ladder down isn't a good option. It puts huge torque on the person holding the upper portion of the ladder and risks damage to the building.
A single fairly strong person can safely stand and lower a ladder by simply placing the ladder base against the wall our foundation and walking it up from underneath, or by backing away.
Folded as in a folding ladder? Or as an extension ladder?
I think the safest method would be to have two people hold the ladder so that you can walk the bottom of the ladder away from the wall while keeping the top of the latter close to but not actually against the wall. That way if the ladder falls, it will fall towards the structure, and not fall far before it stops, resting against the wall.
Folding ladder: Once the ladder is low enough then you can fold it up.
Extension ladder: Release the catches on the ladder while holding the lifting rope and lower it to its shortest height before walking it back from the wall.
The way to handle a long extension ladder safely is to learn how. That sounds tautological, but the point is that you shouldn't mess with it until you've had training and practice , in a safe, open area. If a ladder that long is too much for you to handle, then leave it to the experts.
If you want to learn, here are a few pointers.
1) Make sure the rope is clear of obstructions and that the pulley runs smoothly.
2) Keep the ladder close to the house when raising it, and keep it dead vertical while raising it (not easy). Once it's long enough -- which is to say well above roof level, rest it against the roof and slowly pull the base away until it's at the recommended angle.
3) Before stepping onto the ladder make sure that (a) the rope is tied to a rung as a safety factor to avoid accidental telescoping, (b) the ladder is not tilted to either side, and (c) the ladder's feet are solidly seated on the ground. I recommend a base stabilizer, which is a roughly U-shaped bar that bolts to the ladder and provides outrigger feet to stop the ladder from falling sideways.
To lower the ladder, reverse these steps.
It sounds like you need more than two people (or some special jigs) to handle the weight safely.
Two people can hold the ladder. One person controls the rope, using his body not just the forearms to pull and then gently let out the rope. That's three people.
The ropekeeper can use his body as a capstan. His own weight, not his arm strength, holds the weight of the ladder-half. Let it slide out with friction against your trunk, or turn in place.
