Reputed to be intimately familiar with every last item within his hoard, Smaug instantly noticed the theft of a relatively inconsequential cup by Bilbo Baggins. Had he been able to defeat the barrel riding burglar, would Smaug have known what he had and be able to lay claim Sauron's One Ring?
Probably not. Dragons are a lesser order of creatures, and since Sauron is both a Maia and master of the Ring, in any contest between Smaug and Sauron, Sauron would have prevailed.
Gandalf's primary concern when organizing the Quest of Erebor was:
The Dragon Sauron might use with terrible effect.
(RotK, Appendix A, Durin's folk)
Smaug is therefore clearly subservient to Sauron.
Smaug probably would not have known exactly what he had because
(1) There is no indication any part of his body was small enough to actually wear the Ring, and
(2) Even Gandalf, surely more learned in ring-lore than Smaug, had trouble identifying it from afar.
Thus while he may have been inordinately attached to it--the desire for the Ring works from afar--even if Smaug knew all the relevant details of the Rings of Power, he probably wouldn't have guessed one would land in his lap from the exploits of a bumbling burglar. And as he would have prized it, he likely would not have breathed fire on it (as that would destroy an ordinary gold ring) and thereby revealed the writing.
So it's possible, but relatively unlikely.
The ring is somewhat sentient. He also wants to reunite with Sauron, we could say that he's able to instigate more or less anger or desire on different targets.
If he ends on the hands of a powerful being (such as Gandalf, Saruman or, on a lesser scale, Galadriel or Smaug) it would be more difficult to him to reunite with Sauron. Being attached to lesser beings (humans, hobbits, orcs...) would be easier to attract them to Sauron, eventually it would be easier to make them to be tracked and hunted by Ring wraths or even by regular orc army.
I think that the ring hides itself from beings that could be difficult to overpower and is more comfortable being ported by "lesser beings". He just underestimated hobbit's lack of ambition.
Well totally agree with that. I never thought about the ring avoiding powerful beings and seeking for average bearers, but now it makes all the sense; remember in the Fellowship, when Gandalf asks from the ring to Frodo and it is said in the book about not only Frodo's, but also the ring's reluctance to pass to the wizard's hand? Now, no matter what poor readers says, Sauron is not the only one who could control the ring. He is the main one and for sure the one the ring wishes for, but the list of potential masters is pretty big. Saruman, Gandalf, Galadriel, I bet any of the Eldar or Istari or some sort of immortal/supernatural being (as Smaug, the stupendous or the Balrog or, why not, The Watcher in the Water, depending on its real nature, never clarified) would be able to reclaim it with great chances of overwhelming Sauron (that is stated by Elrond himself). On the other hand men like Aragorn, Isildur, Boromir; they would be able to extract power from the ring for a while, to control it a bit... but after some time, long or short, fall under its corrupt influence and yield it to Barad Dur.
Actually, the list of potential ring masters is small, Sauron or Gandalf. Source: Tolkien himself, in a letter to a fan written sometime after the LOTR was released. Tolkien basically stated that the only being in Middle Earth Sauron would not be able to take the ring from was Gandalf. He then went on to scribble something about Gandalf becoming a jerk while wearing the ring.