Jiffer,
CC is about 15 years old, and yeah, it was moribund until about 2005(like when moi showed up from the east coast).
We do have Insurance through the LAB. One of the things I pressed real hard on when I was on the board. The waiver forms are required by the insurance company. I would definitely not organize any thing without it.
A couple of other words: what are trying to do? as a club , you're open to the public - you have no idea if the guy who just bought a huffy from walmart yesterday is going to show up on the 20+mph paceline. If you want to go for the big tent - which is what we did - beware that you might spend a fair amount of toddling along. about 10 years ago , I was the Secretary for RABA (tulip's club) - back when the heart of Virginia was the Lake Anna Century. I think i rode to Ashland and back at a 10mph pace at least once every 3 months but it will push you outside the usual circle.
A lot of work - but of a lot of rewards - the question is it worth it to you?