My personal opinion is that we aren't judged for bailing. In fact it is sometimes a possible life potential given the stage we are at with a life lesson. It's never encouraged or wanted but sometimes the odds are stacked against us and our human brain sees no other options to fix our troubles. And that is the point. Suicide itself isn't the issue. Suicide is one solution to a problem we perceive is insurmountable. Some people resort to other solutions like drinking, running away or even homicide. As with any destructive driven solution, after we have committed suicide we can appreciate that it isn't a solution that solves anything and only serves to cause tremendous pain and suffering to our loved ones left behind so on top of regret for giving up we may also feel guilt and shame for hurting others but we aren't ever judged by anyone but ourselves and maybe some humans but never by spirit. It's understood how hard this experience is and no one is ever forced to take on a difficult life nor cast aside if they fail to be able to tolerate it once in it.
As for the lesson getting harder after one has suicided I suspect that would depend on where the soul is at and what the soul chooses. Lessons get harder in an effort to wake us up. Humans can be very resilient and adaptable and can learn how to live under very harsh circumstances. The status quo is often preferred over the unknown so we can turn a blind eye to our troubles because facing them is scary then living with the pain. Especially if we have learned how to suppress our feelings. So the ante gets upped or better said, we choose to up the ante as a means for drawing out the pain we so deftly learned to control so we can deal with it. But if we are already in a state of abject pain odds are we may not choose a worse life but maybe even one less painful to give us a better shot at sorting our human self out.
The truth is our soul isn't damaged, broken or unevolved. It's only the human perception that misleads us into believing those things and it is the goal of the soul to shift those perceptions so that more of its true nature can be expressed in the human form. But a human brain that is wired for survival can get caught up living in fear and it's a challenge for our soul to break past that bodily instinct. But in the process of realizing it's true nature in the human form we may make unhealthy, unhelpful, unloving choices to fix and/or solve our troubles until we finally see the only real solution is to throw love at it. Life is a process of trial and error. We will fail many times in the process of learning what works by experiencing what doesn't work because we only have an appreciation for what does and doesn't work by experiencing it for ourselves. At least that's my perception of things.