Andy, you are very welcome to come up with me as a passenger before you try a run up. If I'm not running my 4/4 I'll be taking it fairly gently! I've been up a few times and as Howard says, it's quite a deceptive hill...no run offs if you lose it and some hard banks to hit. However, its not a competition and I'd suggests giving the car a lot of welly and noisy wheelspin at the start....to impress everyone, then take it at a pace that you feel happy to. You can give it plenty of welly after the last bend on the run up to the finish line.
As far as insurance is concerned, it depends on your insurer. I do mine through Headley and they cover me for no additional premium if it is an untimed run and there is no competition element. I just need to advise them of each event.