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^^ Incompetence is likely to be Dr.D's problem. :-)
The shuttle has the same clever gearbox that was fitted to the later Technic car 8880 with the gears always meshed with each other, but using the driving ring part, 6539, to either engage the appropriate gears or allow them to spin freely on the axles.
(Sorry if I've used the wrong terminology.)
With the V-19, I finished the model, and the landing gear just didn't look right in terms of the angle the ship sat at, it didn't seem to compare with the box picture, I tried to resolve it by rebuilding and following the instructions more carefully but still couldn't work out what I'd done wrong so I gave up.
Actually, I remember now I also made a few mistakes in the motorised AT-AT internal build as well, that was a PITA to correct.
Looking back at it now, the set was more exhausting to build than difficult; I guess I was so young it just seemed impossible to me.
It's still probably one of my most rewarding builds, both in spite of and because of it's complexity.
The biggest pain I have had is with the emerald night .. trying to ensure you are using Drk Gry instead of black.. I am guessing it is not much easier for any new sets.. Did Lego say they were going to address that as well?
Otherwise a pain set is the larger pirate ships, at least the Black Seas Barracuda and Skull Eye Schooner.. LOT's of plates in a certain order and set up a certain way... it can be a pain.. Once you build them you are no hurry to take it apart...
After that I'd say the Portal of Atlantis set and mostly I'd say it was time consuming vs. hard.
Hard to build for me also comes in the form of my cat laying on the pieces as I open up a new box and demands that I pet her rather then play with the lego pieces.
My most frusturating set to build must be the BIONICLE (A phase I passed) Vezon and Kardas. Technic is not only frusturating to build, but a nightmare to dis-assemble. It was a few years later when I realized the money and time I wasted on Technic. The problem I had with this set is the stiffness of axles and axle joints, plus the fact that many parts had to be forced into pegs, axles, etc. Set took me a day.....
The Taj Mahal just shy of 6000 pieces:
The Eiffel Tower looks pretty repetitive:
And the Statue of Liberty is almost entirely one color:
These all look like pretty repetitive builds. I can imagine some steps in Taj Mahal might be like "make this window part 20 times". Ugh!
I don't think any Lego set is hard to build for an AFOL, per se, it's just a question of time, patience, and whether the build is actually fun or not. I suspect that there is some large Technic set that might put someone off, but I think people only get into Technic if they're really technically oriented and into that sort of thing.