"How good is the simulator? Does the simulation match what actually happens at the machine or are there differences?"
The only way a simulator will ever truly match what actually happens is if the simulator verifies the actual G code. This is why a product like CG Tech's Vericut exists. I know of no other product that can match Vericut. Vericut is in a class by itself both in functionality and in the high price they charge for it.
"How would you rate the help files and supplied documentation?"
Anyone can download them for free from the Solidcam website. I'd rate them far better than most of the CAM supplied documentation I've seen. Their use of video is also outstanding. I'd also rate them at the top when it comes to answering e-mail and being honest.
I don't use Solidcam right now but I hope to be using it soon based on what I see in the upcoming release which is supposed to have a major speed increase and toolpath editing as well as the new iMachining.
There are many parts of Solidcam that are extremely well thought out. Suggest you watch the Solidcam 2008 video done for drill recognition. One spotting tool, many different sized holes, no need to create geometry just to get the chamfer z depth right and all done in just one operation. Solidcam is one of the few companies who actually can do drilling right and who have a easy to use interface that makes managing drilling very easy. One might make the mistake of thinking almost every CAM company would have this right by now.
I saw your post on the other forum. Nice job on revealing how screwed up CAMWorks really is. Very few people know what you know about CAMWorks. Start a blog and really make a difference... I did.