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The thing is HUGE when displayed on its tall stand with wings folded down, it looks more like an accurate model kit than a Lego set, and the rather complex gearbox with tons of Technic pieces for folding the wings was a sheer delight to build.
My perception is that this kit is not super well received, which I simply can not understand! If you don't have one, buy it while you can in brand new condition for a reasonable price from Lego! If only I could still get a 10179 in brand new condition at the Lego store for $499!
I will never part with the Imperial Shuttle and it will remain built and on display forever!
I was thinking about breaking down all my Star Wars on display (Slave-1, UCS AT-ST, TIEs, etc) to make room for my new sets to be displayed, but the IS will never be taken out of rotation (along with the growing block of Modular building). Which brings me to my foremost concern, preventing yellowing of the pure white since it will always be on display.
I still remember some 30 odd years ago, when I got it for my birthday - happy memories, interessting build, conversation piece, classic LEGO, functional technic, a model of a real car (VW Beetle), and an oportunity to teach someone about gears, suspension and differentials.
If I had the 8880 - competition would be fierce ...
I would most struggle to part with the brick i have stuck up my nose... though not for want of trying. (only joking... i never tried to remove it). (Joking again)
I'm surprised at so many new builds being listed - particularly the sealed in box one.
For me, while all the modern stuff, licenses, UCS's, modulars, etc, are amazing, they're all just examples of what LEGO can do. BUT none of the ones I own really have any emotional connection for me (beyond the obvious enjoyment of... well, enjoying them). If i was forced to, i could probably sell any or all of these modern wonders, and be quite content.
But I think I would have most difficulty parting with one of my earlier childhood sets, that began the whole affair, and helped build so many hours of play time (even though they're all mixed up in an old box, and some of the parts are probably cracked, warped, missing, up my nose, etc). Which one... phew, toughie...
I agree with @legomatt, the sets I would find it hardest to part with are childhood sets. My 6090 Royal Knight's Castle may not be the best set in my collection, but damn it I can still remember building it on Christmas morning as an 8 or 9 year old.
For me it is something simple. The S6 CMF Roman. There may be no build to it, but it is something I have waited for, for a very long time. I have one on my desk at home, one on my desk at work. I have sneaked one on to the dresser in the dining room, and I don't think it has been noticed yet.
As an AFOL, from an aesthetic perspective, I'd have to say Fallingwater http://www.brickset.com/detail/?set=21005-1 is the most pleasing to look at. For build enjoyment it would have to be Green Grocer http://www.brickset.com/detail/?set=10185-1. As a Lego investor, it would have to be my MISB Statue of Liberty http://www.brickset.com/detail/?set=3450-1. I realize buying as investment means that you do plan to part with it eventually, but that one will be the hardest to let go.
But they are all equally hard to part with. :)
But I'm somewhat limited on space for my collection, so I will likely end up selling it within the not too distant future to make room for the latest sets I want. I don't like the idea of packing it up in a box and stashing it away, as that seems to border on hoarding, and I know I would not realistically ever build it again if I did (sort of boring building the same thing twice). Plus, I can use the sale proceeds (profit) to buy other sets.
I think it would be easy to regret selling some sets like you mentioned, but I think purchasing new sets would ease the regret quite a bit.
and that was the Whirl N' Wheel Super Truck #5590 ... i think that would be the hardest to part with.
I have a few sets that are taken apart and stored away, for just that reason.
Still, that being said, the issue becomes the volume of new sets released. We can't keep up with building current stuff, when would we have the time to go back and rebuild older sets?
The truth is, we wouldn't, nor do we need to. At some point, I expect I'll end up with 50+ used sets packed safely away, I'll look at the closet and go "there is money in there!" and sell them.