It's not so much about good weather, but about peak travel days. It is US's response to peak demand on peak travel days. You will see these late night banks during the summer peak travel season and on holiday peak travel days (e.g. Wednesday and Sunday around Thanksgiving).

To the topic at hand, it's generally doable if the flights are on-time. As with other posters, I rarely book such connections because I will be nervous the entire flight. And, as was pointed out, you never know when the jetbridge will malfunction. I actually had this happen and was delayed getting off the plane by 40 minutes, but fortunately my connecting flight was running one hour late (never happier over a delayed flight in my life).