22 Macgregor Gin Pole pic close up. Also a pic of the roller that is is attached to rod holders attached to the stern rail. Easy set up.
I think you are on the right track.
We are a constant gin pole user and you could make that sweet gin pole so much easier to set up and use.
Make sure mast step tightly bolted.
Put a longer mast step bolt in.
On the bottom of your gin pole put a big U (yolk) with notches on the ends that fit the longer mast bolt.
Instead of using that ratchet strap from the pole to the anchor cleat - use a fixed length strong line with a loop at the end that you can wrap twice around the cleat.
Mount a bail on the front of the mast about 6 feet up or so.
Put gin pole yolk on mast step bolt and lay gin pole down
Reel out your gin pole winch cable to the mast hook to mast bail
Get rid of all those ratchet straps (we used to use them too) you have on the sides of mast. Just use one set and connect them to the bail on the mast and then to your cleats on each side (baby stays). We now use a quick cleat cargo line.
Reel in your winch until gin pole lifts and you get mast tension. Haul her up.
Thats all you need.
Without having your attachment points for your baby stays at the same height as the mast step - they will go slack while raising and lowering.
We fixed that with a simple harness made of line and quick connects.
My admiral can handle this setup alone even in high wind.