All the way up, with no problems! Once we raised the tower, we never lowered it. We were very worried about the various cables, ropes, etc. getting snagged - so we didn't want to mess with it. Luckily, everything worked perfectly the first time.
As you can see clearly in this picture, the lower antenna is now raised up off the top of the lower section. The wire rope isn't visible, but it runs from the antenna up to the top of the third section near the Ring. As the tower was raised, the slack came out of that wire rope, and eventually it started to pull the lower antenna up. As that happened, the 8' rod that the lower antenna was mounted on slid out of the leg of the lower section. When the tower was fully raised, the lower antenna was about 5' up from the top of the lower section of the tower at about 25'. The middle antenna is at about 55', and the upper one at about 85'.
The antenna on the ground in the foreground is Tom's old Telrex tri-bander.