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The first does not actually seem possible, at least in the long term. The Ring has a way of being found and trying to return to Sauron. Short of it being dropped into the depths of the ocean, I'm not sure there IS a way for the ring to be put permanently out of Sauron's grasp. And I wouldn't even be all that sure in THAT case. If the ring still exits Sauron will get his hands on it eventually. Those scenarios may delay it but it will happen.
If Sauron actually got his hands on it right away, that would probably be it for the Free Peoples. I'm not 100% sure that even fleeing to the west would help in the long run; given enough time, Sauron might actually figure out a way to attack even there (he'd be insane to try and attack the Valar on their home turf, but as we have established, if Sauron was truly committed to the Melkor path of Darkness, he might just be that insane.)
Gandalf probably would have stayed until the bitter end. But even that could have a special risk. With the ring, Sauron would have crushed the free peoples with very little (from his point of view) effort. Freed of that diversion and now far more powerful than he had been (not as powerful as he had once been, but still a lot mightier than the Sauron we know from LOTR, presumably on par with how he was when it took Isildur, Elendil AND Gil-Galad to beat him into submission (and only one of them survived the effort.) Under those circumstances. I wonder if Sauron, instead of simply slaying Gandalf, would have the inclination (and bility) to capute him and forcibly corrupt him, If with ring, he would have enough power to simply wave his hand and fill any heart with darkness and evil, or stuff the now spare wraith ring on Gandalf's finger and keep him chained up until it had done it's dirty work. If there is any worse outcome than a world with Sauron in possession of the ring I can imagine, it's one where he has the ring and Gandalf (and probably by extension, Radagast) serving HIM.
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