Definitely check the position of the handlebars on the road bike. I used to get hand pain until one day I was having a new saddle fitted to my bike, riding the indoor trainer at the LBS. The person doing the fitting noticed that my handlebars were at the wrong angle. He adjusted it and I haven't had hand pain since then.

Also different bar tape might help with shock absorption.

So I didn't ride this weekend for various reasons but I can tell a story about a friend's experience. He had two flats in the same tire. The first one happened while he was riding on a MUT. Someone stopped and helped him change the tube. Then he had another flat, was going to call for someone to pick him up when a couple driving by in a Subaru stopped to help. They drove him to a nearby bike shop where the mechanic found a teeny-tiny piece of glass in the tire. I've had a similar experience with a flat caused by a piece of glass so small that you really have to work to find it. Another friend taught me to always line up the logo on the tire with the valve stem to help you know what part of the tire to check once you find the hole in the tube. He also keeps folding reading glasses in his bike bag, a stronger version than he usually wears for reading so he has extra magnification.