I studied Astrology with intensity at time when HPs Maxine was heading the JoS, then for some reasons and personal problems I reduced my studies that are incomplete and my knowledge is somehow foggy.
As I restarted some studies, I bumped into a sinastry online that made me think about Saturn.
I always took Saturn aspecting the Chart Ruler in sinastry as a very bad placement, expecially with opposition, square and conjunction. Recently I read Sermons from HP HoodedCobra about Saturn now always being "bad" in itself, with structure, responsibility and concreteness in itself.
I am questioning the trine and sextile aspects, where one person has Saturn in person A's 2nd house trine person B's Chart Ruler (in person B's 10th, also ruler of person B 10th house), with 1° orb. It seems materially that the relationship is not bad, except the Chart Ruler person progressively reducing and loosing his career as an obvious manifestation, and having to financially support person A. The person B ended up in a less career-obsessed life, that was in truth his goal according to informations from the same person.
I do not know about internal/psychological suffering as I have no way to find out on this.
My question is, based on your experience, is Saturn trine Chart Ruler that bad or is it a somehow bearable aspect in a relationship ?

I think it depends on what sign and house Saturn is in and what planets are involved and what houses and signs they are in.

I am just going to give one example from my personal life.

Neptune is co ruler of my chart and I met someone who had their Saturn on the exact same degree my Neptune. Well this turned out bad I kind of lost faith in Satanism for awhile stopped meditating. This person introduced me to their friends who introduced me to drugs. Both our lives were kind of messed up with this for awhile. This matched the position of both Saturn and Neptune in our charts it bought out bad karma in both our lives and followed that theme.

But if you work on the root issues it can turn out not to be negative. I think Trine has a much better chance of not going bad than conjunct or square.

Now me and my her made a lot of progress we are not involved in this stuff anymore. It's turning into I am her spiritual teacher but all the bad karma and experiences in our lives had to be worked through to get to the point of it being positive.

So really it depends on the karma of each person involved and their spiritual level. I can't see something like Ascendent square Saturn or Saturn square chart ruler ever turning out good though the people would have to be exceptionally patient and mature and there would have to be a bunch of good aspects for this to go good.