I resisted depotting for so long... and I still have occasional twinges of regret when I buy an LE shadow and it's in a cute little pot... but overall it was way worth it. I still love the way pots look... and I know this is silly but I felt like my collection looked bigger when i had all pots, and that made me feel better about having spent so much money on it. Now that everything's tucked away in sleek palettes it doesn't seem like I have as much-- and my collection doesn't look noticeably bigger whenever I buy a new shadow.
I swore I would never de-pot, but when I reached 50 shadows, I HAD to. I had a pretty big traincase with four fold-out shelves, and I could fit twelve pots on each shelf, nice and neatly. But once I ran out of space on the shelves (not to mention that all my other makeup- liners, blushes, lipglasses, etc-- was just piled up in the bottom, very disorganized) I bought four 15 pan-pallettes on a whim, came home and de-potted all of them.
I do miss being able to toss a couple of shadows in my bag when I'm going somewhere-- I feel like they were better protected in pots and I'm afraid to take my palettes anywhere because they seem a lot easier to break-- and I'd be breaking 15 shadows, not just one or two!
Really I would reccomend keeping them in pots until your collection becomes unmanageably large. Yeah you're paying more for the pots, but when you do de-pot you can go get a bunch of lipsticks-- so you're not wasting money at all.