Oh, and to answer your original question...yes, it does get less stressful! Anything done often enough becomes familiar, and with familiarity comes comfort. Doesn't mean there aren't some hairy moments even for experienced cyclists, but if it were constantly stressful and scary, no one would do it!

I do understand your desire not to have to drive to rides. My husband and I can ride right from our house, and it's really nice. I can only do that on the weekends, so once during the week I drive to ride mountain bikes in a local park with a work friend.

Good luck - there are a lot of good suggestions on this thread!