the main thing is that the post is useful.
This.
Though I mostly agree with this, I wouldn't merit any of satoshi's posts, and I don't think I've ever merited any of Theymos's. That isn't because of their post quality, but because I don't think the merits I would give them would be distributed in turn to other members who need them. Theymos does merit posts, but I think he's got far more sMerits than he can send at the moment.
As for typical members I send merit to, I don't check to see what they've done with their merits in the past. For one thing, it would be time-consuming to do that, and for another I just don't care all that much. So ultimately if I know for a fact that a member is completely inactive or a known merit hoarder, I might pass them over if I see a quality post made by them, but I don't have hard-and-fast rules as far as that goes.