Originally Posted by SFO 1K

If you pay the $74 for the upgrade and your flight is 20 minutes late, will you miss your connection? It's possible. Will you complain that you paid for an upgrade but didn't make your connection? One is not directly related to the other. 38 minutes is doable, but not by any stretch a guarantee. Hopefully you will have used the facilities on the plane, because if you stop for those, you'll easily lose an extra 10 minutes on your connection time.

I wouldn't take a 38 minute connection, but if you don't mind boarding last, having no overhead space and working up a small sweat in the process, go for it.