I'm finding this thread way too late and so many things to comment on. Oi! Where to star? Some of this has already been discussed and answered in the thread, but I'm just running down the list of stuff in my head and that way have it all in one post.
1. Why was the eldest son of the steward sent to Rivendell to get answers to a dream-riddle?
I think it's more telling of Boromir's character, in feeling the need to go on this quest to Rivendell and for answers than it is of Denethor. In a cast barb Faramir reminds Denethor that it was he who permitted Boromir to leave. But, as
Calacirya excellently pointed out, Boromir was a hard person to say no to, or overrule, when he had his mind set on something. Boromir's own words at the Council were Faramir wanted to go, but Boromir took it upon himself to go and would not have it any other way:
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"Therefor my brother, seeing how desperate was our need, was eager to heed the dream and seek for Imladris; but since the way was full of doubt and danger, I took the journey upon myself. Loth was my father to give me leave, and long have I wandered by roads forgotten, seeking the house of Elrond, of which many had heard, but few knew where it lay."~The Council of Elrond
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Denethor resisted for a while, but in a less sophisticated way of putting it, I imagine a child whining for that toy to their parent so much the parent finally caves in just to get the kid to shut up. And indeed, as the commander of Gondor's armies, Boromir is the one used to giving orders and having them followed. We see this through the entire quest, when the company is agianst Boromir's opinion of the path, he's rather obstinate and bullish "I will not go unless the whole company is against me."
2. Why did Boromir want to seek out Elrond and Rivendell in the first place?
Again using Boromir's words:
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In this evil hour I have come on an errand over many dangerous leagues to Elrond: a hundred and ten days I have journeyed all alone. But I do not seek allies in war. The might of Elrond is in wisdom not in war. For it is said. I come to ask for counsel and the unravelling of hard words. For on the eve of the sudden assault a dream came to my brother in a troubled sleep; and afterwards a like dream came of to him again, and once to me.~ibid
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I don't think there's a reason to doubt Boromir's words here. He's travelled 110 days alone already and wouldn't mind going back alone either. He didn't leave for Rivendell to get allies, but for counsel and words of wisdom. Now he is rather candid later that while he didn't come seeking help, they do need it and in Boromir's perspective help comes in the forms of weapons and soldiers.
As he travels with the Fellowship, I think he would have been wounded had no one gone to Minas Tirith with him, because he came to view them as friends. And since his City is hard-pressed in being threatened by war, he would have welcomed to have them as allies. But that's due to the situation changing from the reasons he originally was seeking Imladris.
3. Why was Boromir permitted to join the Fellowship in the first place?
The simplest reason is the Fellowship was in dire need of strength. Time and time again, we see they are in need of Boromir's strength, and he was right in saying after leaving Lorien they would need his strength to get to the Tindrock.
While Boromir does reveal the idea of using the Ring as a weapon at the Council, I agree with those who said Elrond and Gandalf probably chalked it up to ignorance. It didn't occur as Jackson's movies, where Frodo sets the Ring in the center of everyone and Boromir creepily reaches out for it as he goes on a almost immediately possessed speech to use it.
They talk about the Ring for a bit, Boromir opines "Well doesn't Saruman have a point here in using the weapon of the enemy against him?" The various others say no, no, no, it should be destroyed. It should be remembered that using the Ring as a weapon was also something Tolkien said the bearers of the 3 contemplated (Gandalf, Elrond, and Galadriel) they all concluded it was a bad idea, but simply because Boromir brought up the possibility of using the Ring against Sauron, wouldn't have set off any alarms in Gandalf or Elrond, who we know also contemplated doing the same.
I believe their fears were more on the bearer of the Ring, as the bearer of the Ring would be more dangerous and under constant pressure to use the Ring of Power against Sauron. In the hands of Frodo, if he challenged Sauron, Frodo would have been utterly destroyed and Sauron has the Ring back (but they correctly judged Frodo would be the most resistant to use the Ring for those purposes). If Gandalf possessed the Ring and challenged Sauron, he might have overthrown Sauron, but the Ring would change him into basically another Sauron. But it's not like the Ring sent out this all-corrupting sphere of influence around the Ring-bearer.
Boromir only saw victory through weapons and strength of arms. As he became more desperate to save his City he perceived the Ring as that weapon. Frodo could have been bearing the Ring of Power and applie pies, if Boromir thought apple pies were Sauron's bane he would have tried to use them instead of some silly gold trinket. Boromir's thoughts to use the Ring were at the time, no more than what Gandalf and Elrond had considered as well. The real dangers was in choosing the wrong Ring-bearer, not in choosing the Ring-bearers companions.
I'm out of time, but hopefully more later to discuss on the necessary dynamics Boromir added...and some on Denethor and Gimli.