I really wish I could strive for the depths of realism you true enthusiasts do!
The nearest I get though, is reading the various threads here. As for the actual awarding of medals (the initial question) I've never let SH3 decide who gets what. SH3Commander has that great feature - and is accurate - so I've used it since from the first install. I DO try to take note of any special events though, such as gun-crew or torpedo-room perfomance that resulted in success above the norm. Love reading the threads though - nice to see "gamers" who make full use of a simulator's capabilities!