I had Ultegra 6770 di2 on my road bike last year, and have Dura Ace 9000 mechanical on my road bike this year.
Generally I loved the di2. I'm not much of a mechanic, but I was able to set it up myself and it shifted flawlessly all year - except for a couple of issues:
1. When crossed-chained big to big, it would automatically drop me to the small ring. Had to learn to keep track of what gears I was in to avoid this.
2. The battery (internal seatpost version) leaked and gradually lost power. I gather this can be an issue if riding too often in cold/wet weather. I got stuck in one gear in crits on a couple of occasions. It took awhile to figure out that it was the battery, because when I charged it, I got a green light and the shifting work. I thought it was a loose connection for awhile. Eventually I got the battery replaced on warranty and then it was fine.
In my opinion the weakness of di2 is the battery. It's a single point of failure. If something goes wrong with it (or if one of the connections gets damaged) you're screwed. That's why I'm not excited about wireless electronic. Wireless means that every component will need its own battery, which means there are four points of failure instead of one.
I'm happy with Dura Ace mechanical. Obviously it's a fantastic groupset. But since it's mechanical it needs periodic maintenance, which for me means bringing it into a shop every so often.
In the long run, with the cost of the mechanic's time and the cost of replacing cables and housing, the price difference between mechanical and di2 probably isn't much.
I also have to be more careful about how I shift: when I first went back to mechanical after di2 I dropped a chain in a race, and got dropped from the group as a result. I had gotten into the habit of shifting whenever I like, even uphill under strain. Had to retrain myself.
This is all for a road bike. TT di2 has the obvious advantage of being able to add shifters at the brakes. (Although, on the other hand, you really shouldn't be spending much time out of aero).
So, overall I'm ambivalent about di2. After 10,000 kms on di2 I can't really recommend it one way or the other.
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