Well I tested the winch over the weekend and things were not so good. I could raise fairly well but the pole was always lifting and swaying at a horizontal angle, plus the bottom attachment of the pole was getting caught.
I tried various ways to fix it, but unfortunately it proved too difficult. In the end I gave up, I was just about to concrete in when I thought this is pointless it's just not working properly and in future years, I would be raising up and down sometimes on a regular basis for testing antennas. If it wasn't working correctly now, what would it be like in a few months time?
I really needed something more solid, so in the end after much thought I gave it up. It was annoying as I rarely give in, I like to work things out and repair, but something as important as this has to be right. When I retire in the next few years, this will be my main hobby and I will be experimenting with different homebrew antennas, so I want to have a mast that raises and lowers easily which is permanent and more importantly will last.
So reluctantly, I have now ordered a 35 foot professional built mast with two winches one for lifting the mast upright the other to raise. I've already dug out the hole for its sleeve which is 500mm deep and 1m square. The sleeve is coming sometime next week and I can go ahead and get it concreted in ready for the full mast which will be arriving sometime in late April.
Something's you win and something's you lose!