My two cents on the ring issue...keep it quiet for now. I know that it bothers you tremendously, but I would leave let sleeping dogs lie until AT LEAST after the guy trip. If he reads the LL book it has a segment on rings that just might kick a gear in his head that makes him think. Also consider the possibility that you yourself mentioned about him thinking things through for days and weeks…maybe the ring question is already on his thinking register for the week. Wouldn’t you so much rather he put it on through his own initiative rather than at your request?
"It is not easy to find happiness in ourselves, and it is not possible to find it elsewhere."
--Agnes Repplier, writer and historian