Has anyone here read Graham Greene's novel The Heart of the Matter? The climax of the story turns pretty much on this issue.
The main character, Scobie, is a Catholic military policeman stationed in west Africa during World War II. He is, not to put too fine a point on it, a guilt-ridden wreck, even though he has nothing particular to feel guilt-ridden about. Mostly he's just deeply conscious of all the ways he's failed his wife, his friends, his colleagues, and the people who, as a policeman, he's supposed to protect. After taking a bribe (he needs the money to send his wife on a much-needed vacation) he winds up having an affair, and he just goes to pieces and decides to kill himself.
It's a bleak decision: He decides to do it not just to get himself out of the lives of those he think he has ruined; he chooses to kill himself because he knows it will damn him, and he feels he has disappointed God most of all. He wants to kill himself because he wants to spare God any further pain.
The novel reaches its wrenching climax when Scobie, as he prepares the fatal tablets, actually hears (or, okay, thinks he hears) God pleading with him not to go through with it: "You say love me, and yet you'll do this to me--rob me of you forever. ... So long as you live, I have hope. There's no human hopelessness like the hopelessness of God. Can't you just go on, as you are doing now?" But he pushes the voice away.
At the end, after he's killed himself, though, Greene gives it a brilliant twist. Scobie's wife observes that her late husband was a "bad Catholic." This irritates her priest: "Are you so bitter against him?" "I haven't any bitterness left." "And do you think God's likely to be more bitter than a woman?" This doesn't necessarily reverse matters, of course; Greene never comes out and says anything about the final disposition of Scobie's soul. But it's a reminder that behind all the "rules" of theology is the figure of God. It's not the "rules" that are important. It's God.
A lot of people think that God uses the rules the way a policeman uses the law, or an exclusive club uses its charter: He does everything he can to put people in jail, or to keep them out of heaven. Others think getting into heaven is like getting a credit card: if your "rating" is good enough, you'll get an unsolicited offer in the mail. On Greene's view, as far as I can tell, it's much more like getting married, with God as the psycho girl who wants you to propose and will play any dirty trick that's ever been invented to get you to pop the question. It matters less what is in the rulebook than what is in the heart--but that doesn't mean than you yourself know what is in your heart, so complacency isn't really an option.
I don't know what the correct answer is, of course. I just thought I'd toss out a complicating story.