Looks like fun! I've ridden my road bike on roads like your first picture, but I don't like it, and definitely need another bike, so I can feel more confident and ride some roads like picture #2.
Part of the dirt road we hiked on yesterday looks like #2 and #3. Quite a few years ago, I was on a group ride where they were going to take it as a short cut. I had never been there, and although the first part of the road is fine for a road bike, I had a bad feeling. I left the group and rode back to the start...