A BB isn't exactly exciting...
True - just about the most exciting thing a BB can do is not fail prematurely. And I imagine this only becomes a consideration when buying a bike if you have previously owned a bike with BB30 and had problems with it.
I've ridden lots of bikes with pressfit BBs but have had no experience of owning one long-term. And I've certainly never owned a Cannondale. As I understand it, the specific problem with BB30 (Cannondale's proprietary pressfit standard), is that it requires very precise engineering of the bottom bracket shell, and if the bearings aren't seated perfectly, they will wear prematurely and be liable to creaking.
However, my current main bike uses PF86, which is Shimano's take on pressfit, with the bearings seated in composite cups rather than pressed directly into the frame. This supposedly allows for greater tolerance of a less than perfect finish on the BB shell and claims to eliminate the problems of BB30 (and BB90/95 and other pressfit bottom brackets where the bearings are pressed directly into the frame). I've certainly not had any problems with it so far but I've done less than 1,000km on the bike so I wouldn't expect it to be showing any signs of wear for a long time yet.
As for the supposed advantages of pressfit bottom brackets, my understanding is that Trek introduced BB90 to allow them to use a wider bottom bracket shell (and therefore allow things like fatter downtubes etc) without having to increase the length of the spindle. Cannondale's BB30 uses the same shell width as an external BB but has a much fatter spindle (30mm as opposed to 24mm, hence the name) which is supposedly stiffer and is designed to work with Cannondale's Hollowgram chainset. I don't think weight saving is the main motivation for the design in either case, although it is true that pressfit BBs are slightly lighter than external ones. Frames with pressfit are also cheaper to manufacture. Beyond that, my knowledge of bottom bracket standards gets a bit hazy - there are just so many of them nowadays that it's hard to keep up. (To go back to the OP, I think Trek have abandoned BB90 now and use PF86 instead, but it's worth checking.)
I've always been perfectly happy with external BBs - they're reliable and very easy to replace when they wear out. I will be interested to see how the PF86 fares in the long term, but I already know that I am going to need to buy yet another frickin' special tool to replace it when the time eventually comes.