I don’t believe you can ‘play the system.’ Your intentions must be pure, and you must change your life around, even if you have very little time left. Nobody is beyond forgiveness, but it must be in your heart to change. I am far from being a bible thumper, but this is my understanding of it. I’ve often thought of this myself. I’ve worried in the past if there really is a point of no return.

Just getting my own life together precludes me from judging others.

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Consider the parallel passages Luke 17:3-4 = Matthew 18:21-22, both thought to be from the lost Sayings Gospel Q. Where Jesus says, essentially, there's no limit to forgiveness ("seventy-seven" or "seventy times seven" are to be read as a punning metaphor for "infinity").

I don't know about you, but I am human. I make mistakes. Through ignorance. Through stupidity. Through pride. On the wave of an emotional moment. I cannot work hard enough, study long enough, or move quickly enough to do otherwise. I do not have the brain capacity to store everything I would need to know to be perfect, or the neuronal capacity to deliver that knowledge to where it's needed in time. If I am condemned for every mistake, I'd never make it out of the maternity hospital.

What do I then do about those mistakes? If I refuse to acknowledge them, I declare myself at odds with my community. I am "out". If I do acknowledge them, however, I'm asking to be let back in. If I'm allowed. And thereby hangs the bargain. The one who has made an error agrees to acknowledge the error, apologize for it, do what is possible to set matters right, pledge to not knowingly make the same (class of) mistake again. The community agrees to accept the apology, the reparations, and the pledge, and accept the erring member back.

Never mind heaven, or hell. The deathbed confession, in this interpretation, is for the living. It is to allow those who carry on to remember the one who has died as "in" rather than "out". And to prevent the "outness" of the unforgiven individual to reflect on that person's friends, or offspring.