Good points, Noodles, and I can pretty much agree with everything you're saying there.
I hadn't really thought about Roland not even needing to go to the Tower. Once Roland had restored the beams, there was nothing the Crimson King could do. He was trapped outside the Tower with only some sneetches, so really there was no need to erase him either.
Since there are so many different ways something can go, I have to wonder how different each trip to the tower was. For example, in his previous one, he didn't go to sleep on the beach and didn't lose the fingers on his right hand. Or, in an even previous quest, maybe he lost one of the two guns with the sandalwood grips.
Anyway, interesting to think about. It's like an eternal never-ending torture for Roland. It also explains why Roland is constantly constantly constantly referred to as being hundreds to thousands of years old when he really should only be about 38 or 40 years old. He's been doing this quest hundreds of times by now.