I don't use a gin pole on my boat, but I do have an 8' crutch that I fit into the rudder gudgeons, much like you show in your original picture. This gets the mast about 1/2 way up, roughly 45º. I then stand on the cabin top facing aft, straddling the mast. I can start lifting and then start walking backwards along the cabin top, being able to keep the backstay, and both shrouds in view in case there is a bad kink, in which case I can lower and start again. I also have a swiveling cam cleat for my spinnaker halyard, so I clip that to the stemhead fitting, and once the mast is up, with minimal pressure towards the front with one hand, I can pull the spin halyard tight and cleat in the cam cleat. Now the rig stays up while I futz around with pinning the forestay. I have never been the kind of person who can stand in the cockpit, lift the mast, somehow jump up on the seat, then the cabin, all while keeping the mast in line so it doesn't bend the sh**t out of the mast step hinge. Facing forward and walking a mast up works in an open daysailer, but not when I've got the cabin. I'm thrilled that I discovered my method, and I try to teach it to anyone in our club who needs help.