Well, the one really big beer I ever brewed, a barleywine brewed in 2010, carbed up perfectly (no extra yeast, sugar dialed in moderately at most). It had other flaws, but not the carbonation, so this issue wasn't on my radar, or I would have done one of my tried-and-true recipes in the 6% - 7.5% ABV I usually brew in.
I was so close to kegging I had all the parts picked out, and had called a local sporting-goods store to confirm they refilled tanks. But to be honest, for over two years I have been bribing myself through the graduate program with "if I make this goal I will give myself the luxury of doing X," and kegging has been the prize for defending my dissertation proposal, with the understanding that newbies do sometimes struggle with kegging and I might need to devote time to puzzle my way through it. Part of it is the reward factor, and the other part is superstition. But those cute little kegs look mighty tempting.