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If I'm doing one of my own rides, for 10-15 people then I'm not particularly concerned about insurance, and don't worry about it, but if it's 50 people then I would be.

I went on the same CTC Ride Leader course just before Christmas and basically they're just trying to get people to get out on their bikes and ride, either setting up their own CTC affiliate group (if people want the insurance/rules) or doing their own thing, and suggesting ways to get people to enourage others to cycle. It was quite a good overview in fact. The handbook provided, which is also available somewhere on the CTC website wasn't presecriptive but had lots of good pointers about things to consider and certainly wasn't a H&S driven document. In fact I was quite surprised the CTC had produced it!

In respect of CTC ride leader insurance, an individual might have a limit imposed on them for rides- I know their Off road/mountain bike course limits the leader to only 12 other participants. However, anyone coming on a FNRttC, where we've had over 100, can be reassured in knowing they're covered.
 

Dogtrousers

Kilometre nibbler
We are all in danger of disappearing up our own fundaments with anxiety, rather than just getting out and cycling about together having fun.
This.

Which is not to say that I'm immune to this anxiety, quite the opposite.
 
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