For the completest, here is full documentation on how to get your bike and tour gear from Cambridge, MA to Berlin with only some minor, repairable damage.
Assemble your gear. I find it useful to spread my stuff all over the floor in a giant mess that your soon-to-be-housesitters have to walk over on their way to the office you make them use as a bedroom until you leave for your trip.
Take apart your bicycle. Remove all the accessories you would never be caught dead with on your city bike. Then, using the magical S&S Couplers, break the frame into two sections in preparation for Step 3′s contortionist exercise.
After placing padding on all painted surfaces in attempts to limit cosmetic damage, carefully stack and interlace the pieces into the carrying case (in this instance, the Co-Pilot wheeling case). From bottom to top, I opted to pack in this order: front triangle (with handlebars removed but cables intact), rear wheel cassette down, rear triangle, handlebars wedged into place, front wheel. Next, smaller accessories (lights, axles, tools, etc) can be stuffed into available spots along with a large number of extremely cheap Target towels for padding.
Assemble your bags and call a taxi for the airport. Be prepared for strange stares as you wrestle with three giant bags (also, be prepared for the somewhat reasonable $200 extra baggage fee for bringing three items on the Lufthansa flight even though all three are overweight).
While mostly successful, turns out this packing system had a few flaws. Noted minor damage includes a bent front axle (easily replaced for 12EUR), cosmetic damage to the down tube likely from a rouge cable which burrowed under the pads, and a dent to the front wheel (rideable, but hoping a Berlin bike shop can bang it out and true the wheel). Also, the front derailleur lost alignment. I spent an hour trying to calibrate it myself, but going to let the shop mechanics dial it in on an actual repair stand.
Overall, a fairly successful transport. With the baggage fees and repairs, probably a total cost of $300 to get the bike and gear to Europe. Will provide updates once the bike is back from the shop.