1. Who's more enduring as a ring bearer?
- kind of need to define 'enduring' here. Two basic aspects. Longevity and the sense of 'suffering under pressure/pain.' Longevity of course goes to
Bilbo. 'Endurance' in the sense of suffering of course goes to
Frodo.
2. Would Bilbo have made it to the Mount Doom and would he have thrown the ring?
- Difficult to say - speculation. My opinion tends to "no." He wore it many more times than Frodo - and it is well noted his original possession of it included some deception for personal gain. Not telling the truth about it in the beginning, so he would 'look better' to the gang - then always wearing it to "hide himself" from those he didn't want to encounter. Selfish motives all around. Thus, his ultimate inability to 'easily' part with it - it was working on him all along.. (Note: Bilbo was, by and large, a rather 'noble' and honest fellow. But he did have a bit of a selfish strain to him, not opposed to a bit of self-centeredness from time to time. That was
the ring's "hook" into him.)
. Then we need to take into account
Sauron didn't know about the rings recovery for quite a few years, so his 'thought was not bent upon it.' Bilbo suffered none of the added pressure of Sauron's intensity. It's noted the ring "seemed to grow heavier" all the time Frodo bore it - and Bilbo later realized 'the ring had grown beyond him" even without wearing it again.
3. Could he have endured the entire journey?
- Given #2, my opinion would be "no." Many reasons. He was older, though still being maintained a bit by the ring. The growing "weight" of the ring would have been harder for him to bear. And too, he would have had no "
Sam" - though one could speculate perhaps a Frodo would have stepped into the Sam shoes. But lastly, though
Gandalf had a suspicion about this which is why when Bilbo spoke up, Gandalf denied him the offer - he wasn't the Providential choice, and without the aid of Providence, there could be no success.
4. How do you see each of them's "wearing style" and purpose of wearing the ring? 
- Bilbo's 'wearing style' was generally personal and selfish. Frodos was honest, and wary, since he was fully aware of the ring, what it was, and could do. (So was Sams, both of them only putting the ring on for protection, and accomplishment of the Task.)
5. Who's more attached to the ring? Who bears the shadow more lightly? Frodo has a more difficult task because Bilbo wore it at home but Bilbo wore it for a longer time and in less unconditional circumstances. And Frodo's higher goal did serve as a fuel to endure it and shield against temptation, yet worse the curse than if just worn at home.
After all, Bilbo did give the ring to Frodo.
Frodo offered it to Galadriel but had she agreed - would he have made the Bilbo face and would he have endured handing it over, SINCE he didn't really throw it - Gollum fell.
- a number of pieces to this. My opinions: Bilbo bears the 'shadow' much more lightly, but the 'shadow' is much less a 'shadow' as Sauron's mind is not bent on it.
- Yes, Bilbo gave the ring to Frodo, but only because Gandalf's manifested 'power' at the time exceeded the ring's small hold on Bilbo.
- The same is true when Frodo offered the ring to
Galadriel so impulsively. The rings hold on Frodo was lesser at that time than it ultimately became, the closer he approached to Mt. Doom. My opinion is Galadriel's power, which Sauron himself was a bit wary of, is what brought Frodo to offer the ring, and he would have given it. Even if he had a moment of the "Bilbo face" in doing so - it no doubt had a hold of some strength - he still would have turned it over - UNLESS he recalled the injuncion of his charge, "not to give it to anyone else" at the council. (In other words, a rather honorable 'meeting of the charge' might have been his guide, meaning when actually 'put to the task' of handing it over, he may have renigged on his offer to her, citing the charge as his reason. - still an 'honorable' thing, fidelity to the Charge overcoming the impuslveness of the Offer. And Galadriel would have understood it..!)
In the end of course, he was overwhelmed by the weight of the ring and failed to resist the ring's grasp - but herein lies something always having been a curious note to me..!
The "charge" he was given was never to "throw it in," The "charge" he was given was to "take the ring to mount doom" and "not to give it to anyone else." He fully succeeded in the charge he was given.
It was "providence" driving the words of the charge given, though
Elrond did not know it - and it was Providence putting
Gollum at Mt. Doom to carry out the actual destruction of the ring.
Frodo completely fulfilled the charge - as did Sam. The ring was ultimately simply beyond his "endurance" level, and Providence (
Eru) knew that would be the case.
Some folk question whether Gollum also fulfilled some charge or other, and have raised some objection to my view previously when I shared these thoughts - and that's OK. Having pondered long, I could speak to that again, but it's not part of this question so I refrain here.