And I so hurt for poor Hobbes in that tree and even moreso for Pogo because I know how that feels for him. Have you tried your retrieval basket that worked before Pogo? I know it won't reach as high as Hobbes is, but if he got in it before, maybe if you stuck it up there, he would descend that far?
Yes, did that yesterday exactly as you describe. Got it about halfway up but he didn't take the bait.
Pogo
Hobbes is trying to tell you that he is not happy with something in the House.
My bet would be that he needs a place or two where he can get up near the ceiling no matter how low it is. He needs a place to feel higher and safe. It does not matter that he is safe - it is just a cat thing that they all need. Every Cat needs a scratching post and some place up high in any house.
Do maybe two places with some shelves or anything else you can think of to build, where he can get up near the top of the ceiling.
Especially since you can't fit a cat tree.