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Saya cover + drawer for the Masamoto gyuto.
of those, masamoto hands down
but get this instead
http://www.mtckitchen.com/p-768-takamura-hsps-gyuto-knife-21cm.aspx
They are both awesome, you really can't go wrong. I have the black handle Takamura and is the best knife I have ever owned, though out of your stated price range. The red handle one is cheaper because it uses less total steel, but it's the same quality. It's a lot like the Masamoto in that is a "laser", which is to say, extremely thin. This is for fine veg cuts, not for anything hard.
I have less experience (but not zero) sharpening a Masamoto. I would say that the Tak is probably easier. I bought this stone:
http://www.mtckitchen.com/p-1638-kitayama-sharpening-stone-for-knives-fine-grit-8000.aspx
(among many others) and lately it is the only one I have needed to restore the edge. It's rated at 8,000 grit but knife geeks say that when you use that little buffer stone (nagura) to prep it, you get a range of up to 12,000.
The other thing I would say is that the Tak is a 50/50 edge, but the Masamoto performs best at 70/30, which is more difficult to do. You can learn how, but it's trickier and will take more practice.