In regards to focusing on chamois coverage and position, I'm not sure how to go about doing that to be honest. None of the brands I mentioned in my original post show where the pad is in the bibs and some don't even show an image of the pad at all. If I could get my hands on them before purchasing that would be great, but there isn't a store in my state at all that sells what I've been looking at. The one local bike store just has some cheaper Bontrager in stock so I'm left to online purchases.
I have a pair of Desoto Riviera tri shorts and I really liked them, but I don't really enjoy shorts any more after trying bibs (Przewalski which are "fine I guess"). My gut instinct was to buy the Desoto 400 mile bibs based off the shorts experience, but I don't see much buzz about Desoto outside of the triathlon world so it made me a bit hesitant for strictly cycle oriented apparel. It concerned me that I might should open up my options and here I am.