I have been leading rides both on and off-road for more years than I care to think about . Some of these have been organized by myself to a like group of people/friends and others have been formal club rides requiring waivers, etc.

In either case, email lists are the best communication. As the ride leader, you get to determine if the ride is/is not happening for whatever reason. After some amount of time, your group will take on a life of its own, and if you can't make it due to illness, appointments, etc., someone else will step in so the ride is not missed. Weather (rain/storms) always canceled.

I would be careful about the painting on the road. Around these parts, permission is required, and can be difficult to obtain, especially if a town doesn't have a high tolerance for cyclists to begin with.

You've gotten some great advice. If this is what works for you, and you want to lead, go for it! I've met some great friends/riding partners this way.

SheFly