Speaking for myself, I think Ai is pretty high on the list. I'll also put my girl Natsu on that list ( she's great). Finally, Nana gets my vote, she got that 'cougar like' quality about her.
Love your game plan, two ladies per day. I only do that when I'm in Phuket. My US dollars goes farther ;-) The only problem I see is that, alot of the ladies have regular day jobs.
Quick comment on the drinking part, is it me or are the drinks in Tokyo a little on the weak side. Last year after drinking a 'Long island Ice Tea' I wasn't even buzz.