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It's interesting that you should mention the element of "luck" in the riddle game, Lhuna. Both Bilbo and Gollum were lucky, I thought at first. But closer reading has brought me to agree with the idea of Bilbo's luck.
The first answers were easy on both sides, warming up, so to speak. Then Gollum had to dig deep for memories of sun and daisies, as well as for eggs - not really the result of luck, but of thinking. "Fish" was Bilbo's first 'lucky' answer, but the real luck was with "time", which was spoken unintentionally. Divine intervention? Possibly...
The "pockets" riddle was also spoken unintentionally, as a question to himself. Gollum could have passed over it and demanded a genuine riddle, but he accepted it. Did Bilbo have help from 'above'/'outside'?
As a matter of fact, wasn't the pockets question absolutely necessary to the further development of events in LotR? If Gollum hadn't realized that Bilbo had his ring, would he have left the caves to search for it, or thought it must be in there and looked even deeper for it? And if Gollum hadn't left his 'home', would the ring ever have been destroyed?
Yes, I too make the connection with the bigger and later story when I read The Hobbit, especially this chapter. But that's not surprising - after all, it was revised to fit those 'future' events!
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'Mercy!' cried Gandalf. 'If the giving of information is to be the cure of your inquisitiveness, I shall spend all the rest of my days in answering you. What more do you want to know?' 'The whole history of Middle-earth.. .'
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