I think there's a lesson here in learning to recognize when you're doing something in a way that's unnecessarily complex. Does your son prefer to create a complex solution (because maybe it's enjoyable?) or does he just go the complex route naturally? Somewhere in-between?
IMO, learning to recognize that there may be an easier way to see or do something that appears to require many steps and conversions is a fundamentally important skill.
I agree with Zen Scanner that some very mathy people intuitively see many math problems in a way that's fundamentally different from most other people. But that doesn't mean that mathematics (or whatever subject) is an either-or proposition or that one way is universally better than the other. There are times when being able to visualize something in a complex way will confer a huge advantage. But the thing is that there are also times when this same approach will cause a huge disadvantage because it makes something basic way too messy. (And of course the reverse is also true for always seeing things in simple terms).
Maybe you could try to teach your son how to see both sides of the coin.
He seems to gravitate toward the complex rather naturally, although I would also say he tends to prefer it in some cases. His GT math teacher spent a lot of time last year working on getting him to see how other people solved various things, so he would have more tools in his box. She will not be there next year, so I'm hoping the next teacher will continue that.
I drew that picture in my head as well, a line of trays (and drew them as a 5x5 square), but it took me a while to realize that every tray had to have something on it -- if that weren't the case, there were quite a few possibilities.