My understanding of the will of The One is that it is not of the same kind that a will of a human or another being with soul. The One does not possess an ego and cannot make decisions. Its will is Sauron's own potency detached that makes an impact on other's wills and minds in the way similar to a magnet pulling other magnets and everything made of iron. The Ring drives and gets driven.
It stayed almost dormant with Gollum since he had got subdued. The return of Sauron, probably, activated it so it allows Gollum to loose it. With Bilbo it is on the move and the direction is right but suddenly Sauron gets driven out of Dol Gudur. At that moment Sauron wants to find The One but is concerned with a possibility that someone else, mighty enough, can find it before he knows and this must have affected the Ring's own activity. At the same time Bilbo keeps his vigilance and doesn't allow the Ring to get lost on those occasions when it could be driven to evil creatures in close proximity (the Battle of Five Armies is probably the only such occasion as Smaug is not an option for the Ring).
That's how I see it. The Ring did not make a decision to abandon Gollum but the situation had ripen. It happens that some parasites in course of their natural development make their 'master' weak and slow - that makes the 'master' an easy victim of a predator who, in turn, becomes a new 'master' - a smart strategy but it doesn't mean a particular parasite make a decision to change its 'master'. With Bilbo the situation in which The One could make a progress towards its Lord just never happened, that's why, in my opinion, it remained with Bilbo for quite a while.
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