There are detailed instructions on the
Bergey website that tell you how to raise their towers. Though not as tall as yours, they're pretty heavy and the same principles will apply. You don't have to buy a Bergey to learn a lot from them!
Their manual suggests that once the tower has been raised to the balance point, but there's still tension in the lift cable, a person should go to the gin pole and lower it by hand to the ground.
Hmmm... not sure this would work if the height, hence the forces & weights, are doubled. Going with the back winch sounds like the better plan.
Isn't this your first tower Smoggy? This may have been hashed out in another thread, but could your mill do almost as well on a 50'?