Oohhh, a new can of worms! ;^) This is sure to generate some passionate debate.
Well, I am on my fourth Starmaster, so I want to admit my bias right up front.
The Obsession may look a bit better than the Starmaster, but they both look pretty darned good, IMHO. The Obsession is brown, the Starmaster is oak. A matter of preference, I suppose, but I like the look of my Starmaster better. Then again, I didn't buy it to be furniture.
The Obsession, IMHO, has smoother motions than the Starmaster. This can be a good or bad thing. I have seen Obsessions windmill in a breeze that the Starmaster laughed at.
I prefer the triangular configuration of the Starmaster's trusses, as they make it faster to set up.
I don't like the sling that the Obsession uses, as I have seen Obsession owners have to recollimate two or three times during the night. I have seldom had to recollimate during the night after my initial collimation. Also, on the subject of the mirror cell, I love the fact that I can remove my mirror and transport it separately in its own transport box. It makes the whole thing easier for those of us with back problems to own a larger scope. I recently had to help the owner of a 20" Obsession unload his scope out of a SUV and just about ruptured myself.
I like the thinner mirror, as it cools down much faster. Regardless of what the Obsession website says, the thinner mirrors in the Starmasters (D. Kriege does not mention Starmaster specifically) do NOT show astigmatism because the mirror is supported properly, the way the mirror maker supports it for testing.
I know that there has been much said about Carl Zambuto's testing methods, and his claims for Strehl and wavefront error, but I have now owned three CZ mirrors and can tell you that the proof of the pudding is in the eating. The deep sky views through my 14.5" Starmaster beat the views through any other telescope in my club, and on nights of good seeing, the planetary views do too. Having said that, if the Torus mirror is good, then I think that one would be splitting hairs to tell the difference in actual views at the eyepiece through either one. Once one gets into the area of premium optics, the views should be outstanding no matter who the mirror maker is.
I like the fact that Rick tests each scope throughly, under the night sky with eyepieces. He not only checks the mirror, but the goto/tracking system if it is ordered, and the whole scope for any flaws, etc.
Rick's customer service is second to none. I bought my first Starmaster from Rick six years ago, and I still get Christmas cards from him and his family. I can call him anytime at all, including weekends, to discuss anything from collimation to the weather.
Hope this helps!
Doug
Midway, FL