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I know this isn't really the answer you are looking for but if it were me, I would get a second bike with super-low gearing. I have a Campy triple bike that I use on the hilliest routes. I know you really want to stick with Di2 but now that you are getting older you should be going retro and eschewing that newfangled electronic stuff anyway
 

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Excellent point. Purchasing another bike is a lot less expensive than purchasing a crankset.
Of course its not but having a second bike has lots of benefits. Plus its seems like there are a lot of compromises to just get a somewhat lower gear (25 vs 28 gear inches)
 

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I've got so many bikes I have to give some away to keep out of divorce court. (Unfortunately one was my Trek 520 touring bike, which had a nice granny gear.)

I've already put a 46/30 on my Bianchi.

I'm interested in the best option for this particular bike. I live in steep hills, and also like to ride it off-road, so really this one is the "second" bike. As for compromises, one point I was trying to make was that the ONLY thing I would lose is the 50/11 gear, which I have almost never used. Given how little compromise there is, I am rather surprised Shimano and other big brands don't have 46/30 crank offerings. (I got the Di2, BTW, because it was bundled with hydraulic brakes at the time. However, I am not at all sorry. It really is nice.)

I was hoping just to get a discussion going. The only (implicit) question I have is whether I have missed other options.
A 46/30 is probably good option for lots of folks, but I think the OEM market will continue to drive the options.
 
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