I don't doubt the Japanese could keep the larger convoy together. The question becomes what would happen if they are discovered, which is more likely because it's going slower.No one is saying it would be totally impossible. However the difficulty of adding so many ships (some of which will be commandeered civilians) will increase the complexity of the operation by an order of magnitude and decrease the convoy's speed to such a degree that the chance of something going off will be incalculably higher, especially if they take the snaking approach route they historically took. (A more direct route will go right past some American bases)
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Just marshaling all those vessels off the kuriles will be significant challenge and they'll be at sea much longer. . . giving intelligence assets more opportunities to catch on.
Aside from that, the Malaysia landing force *was* sighted before war broke out and was the reason Repulse was recalled to Singapore. You are quite right that the invasion was successful but the japanese did lose men due to rough sea conditions and the RAAF with much fewer air resources than would be available on Pearl did significant damage to the transports.
The most difficult task would be to win the land battle if they get landed. I believe their infantry relied on intense physical training and light equipment during action, so overcoming determined US resistance would be very tough without support and more supplies from the fleet. Even more important would be sinking or driving away the US fleet. Very risky and dangerous, and they'd have to be very successful to be able to loiter around the islands providing support.