How Highly he Thought of You

Look, I really just want to say that if this is a trial based on Yoda's deepest fears and desires, meaning one of his desires is for Obi-Wan to have known Dooku

If this is how Yoda wants things to be, he wants Dooku to still be with the Jedi and he wants Obi-Wan to know him. Yoda knows Obi-Wan would adore Dooku, he knows that if Dooku was still there, the loss of Qui-Gon might've not ruined him so much, because Dooku would be there and maybe Obi-Wan would've been okay.

Look how Obi-Wan doesn't take his eyes from Dooku, he adores him, he cannot stop smiling and he's just so invested in everything Dooku has to say. This is a child wonderstruck by old stories their Grandfather tells them. This is the Obi-Wan Yoda knows he would be if things hadn't gone how they had. He'd be happy, Yoda sees Obi-Wan's suffering and his strength and loyalty to the Jedi, he sees all that and knows Obi-Wan isn't happy, that he carries such a burden, so in Yoda's utopia there is such an emphasis on Obi-Wan's happiness because it isn't fair for Obi-Wan to suffer so much when he's never strayed from the light.

Yoda knows this, and he knows if he still had those two, Obi-Wan wouldn't suffer so.

Think of Obi-Wan's seat on the council too, we know Dooku was offered a seat and that Qui-Gon was too, then Obi-Wan and Anakin. Their entire (disaster) lineage was offered council seats, perhaps because Yoda, though Jedi cannot form attachments, offered Obi-Wan that seat because of how much it meant for Yoda to have one, one that turned out okay. And maybe Yoda looks at Obi-Wan and sees Qui-Gon, he sees Dooku, and his pain is a little less.

One of my favorite things to do are analysis' like these, if you want to see my take on a certain scenes send a request in perhaps :3