1

   "Good afternoon," said a soft voice. Harry jumped. Hagrid must have jumped, too, because there was a loud crunching noise and he got quickly off the spindly chair.
   An old man was standing before them, his wide, pale eyes shining like moons through the gloom of the shop.
   "Hello," said Harry awkwardly.
   "Ah yes," said the man. "Yes, yes. I thought I'd be seeing you soon. Harry Potter." It wasn't a question. "You have your mother's eyes. It seems only yesterday she was in here herself, buying her first wand. Ten and a quarter inches long, swishy, made of willow. Nice wand for charm work."
   Mr. Ollivander moved closer to Harry. Harry wished he would blink. Those silvery eyes were a bit creepy. (Harry Potter and the Sorcerer's Stone)

I’d see you is way more common than I’d be seeing you on this Ngram. What is the latter meant to say? (Does it imply the near actualization of their meeting rather than hope?)

2

Most verbs of perception and feeling—see, know, hear, feel, like, want—are stative and are not ordinarily expressed in the progressive.

One characteristic of statives, however, is that they are ‘non-agentive’. The state which the verb expresses is felt to be an attribute of the subject rather than an action performed by the subject. Many stative verbs have semantic ‘partners’ which express the action of getting into the state: watch and listen for see and hear, for instance. But that still leaves a semantic hole—there is no way to express seeing or liking or feeling as an activity, as something in which the subject actively participates.

A workaround that has become fairly widespread over the last couple of generations is to ‘agentivize’ these verbs by expressing them in the progressive. And that’s what’s happening here. Ollivander is a merchant, a master craftsman and in effect a ‘consultant’. He doesn't merely see clients like Harry, passively, he interacts with them, he evaluates their needs, he advises them. So he quite naturally expresses his expectation of pursuing these activities with Harry not as I thought I would see you but as I thought I would be seeing you.

2

It means that at some point in time prior to Harry walking in the door, Mr. Ollivander had been thinking to himself something like: "Wow, time sure has flown, I bet Harry Potter is getting to be old enough to attend Hogwart's. I expect I'll see him comimg into my shop in the near future."

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