Interesting, Mr. Viennahog. Maybe I read your link to fast but did you say that your left main bearing failed? Sure looks ugly...sorry to hear it.
I would think, based on what I have read here and other forums that for most purposes like tourng and cruising, the straight roller on the 2003 and later would be OK at 95 cubic inches. OTOH, If you are one of those who like to push your motor really fast and do a lot of heavy duty street dragging, (you know who you are!) then I wouldn't doubt that you should go to a tapered Timken roller. The one in my Shovelhead is still good after 24 years!
Funny thing, the dealers are installing 95 cu in kits in almost every last bike they sell these days (except mine) and they never say a word about the left main. Even their Screaming Eagle 103's have the straight roller. Go figure.