$9000 speaker Orangutan or speaker + amplifier

As a reality check, given your current system, have you considered upgrading your turntable first. My view would be that you would get a more fundamental improvement by upgrading your front end rather than your speakers.
Having said that, I have heard the Orangutans on quite a few amps. They are very enigmatic. They definitely open up with tube amps, but I have noticed that even with tube amps they can go from closed in, compressed and unimpressive to open, fast and fluid. The best amps I have heard on the Orangutan's were a small Shindo amp, by a long way. I suspect that if you buy the Orangutans you will need to try amplifiers before buying, otherwise you will be risking matching issues and may be extremely disappointed.
Having heard the Tannoy Kensingtons in the same system as the Orangutans for similar money I would look to the Tannoy Kensingtons.

I have heard both the O/93 and 0/96. THe 96's with Shindo gear in a large 14X20 room and they make large and involving music that is rich and fills the room. I have also heard them in a small room and I didn't like them as much. They are a no compromise speaker that with the right gear and right room might make one feel they have at arrived at a place where upgrades are no loner needed.
I have also heard the 93's in a smaller room with Line Magnetic gear and also thought they very engaging. My time with the 93s was limited so I have a less solidified impression, but the music sounded right.
Hearing all your speaker choices and find the one you like the best. Talk to John Devore. Talk to your dealer.

talk to the several guys in this forum who own 93s and 96s.

I have not heard the Orangutans but judging by Art Dudley's description in Stereophile and knowing what he likes a stereo system to sound like I would go with them. But I am not buying them. And judging by your description of the music you like I would go for the Harbeths....

"The best amps I have heard on the Orangutan's were a small Shindo amp, by a long way. I suspect that if you buy the Orangutans you will need to try amplifiers before buying, otherwise you will be risking matching issues and may be extremely disappointed."

All the Shindo amps are small...?