Flying continental airlines 16 hours. Is it that bad?

I'd definetly take the 5:00 connection. Of course you'll arrive much later, but it helps especially if the flight is delayed. When my family was traveling home from a recent trip, we had a layover in Detroit and since the first flight was delayed we had 15 minutes to run from the far end of concourse A to the far end of concourse C. It would've been nicer if we didn't have such a short layover (it was an almost hour layover turned into a less than 30 minute one). So it doesn't hurt to pick the later flight.