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@Dammit
Just to provide an alternate point of view- I've never had an issue with BB30, have it on the Boardman which was used all through last winter as a road bike and the BB never gave me any trouble.
The issue I thought I had with the Cannondale BB was, in fact, a Zipp skewer- which I wish we'd been able to deduce before messing around with the BB a lot based on their rep, but there you go.
I think that if hte BB shell is machined well you won't have an issue, if it's not done with a high degree of accuracy then you will.
I would run SiSl2 cranks on a nice bike- very stiff, very light, modular so can take compact/standard/powermeter as your preference/requirements change.
But they are expensive- which is why I have three pairs of Rotor cranks, which I find to be fine for the amount of power I produce, and have all the benefits of being modular as well as being able to fit BSA/BB30/BB86/etc.
Finally, I would pick Di2 over mechanical - with the new multishift stuff, adjustable shift speed and so forth it is now doing stuff that mechanical groups cannot.
For example I've left my climbers switch on as I find it really convenient- I had only fitted it for Dalsnibba, but it's handy to have.
I think that if you take some care over the install you can make it look acceptably neat- I took some photographs of the way I have done mine and posted them in the System Six thread.