I haven't ridden a bike in maybe 10 years, and didn't ride much back then. I've recently been training for a long ride (180 miles in 2 days, rest a few days, then return). I started training around 3 months ago (I'd already been doing Stairmaster, treadmill, and weights for general health). So I'm counting 3 months ago as my "first ride."
My answers:
1. 23.5 miles (with frequent stops)
2. 100 miles (stopping every 10 to 15 miles)
3. Yep!