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You might find the cycle understanding you are seeking in house placement transposed over natal Saturn. What I mean by this is to visualize or write down on a paper chart, or if software allows it, a Saturn on ascendant equal house chart. Each 90 degrees of transit travel will be seen at the four angles, the opposition at the descendant, etc. When viewed this way, you'll find that the last quadrant, represented by the last Saturn square Saturn, is found at the MC, or the beginning of the 10th house. Isn't that "career" in the noontime external world?
Perhaps further understanding can be asked to yourself what you were experiencing when you were 22 or thereabouts, and how that time period might be similar in someways to your current situation; albeit with the realization that now you are older, wiser, and more experienced.
Another way of viewing the cyclicality might be that you have disciplined yourself well, faced life's various saturnine challenges in a constructive way, therefore you aren't experiencing its more negative, extreme side. There may be some sense here that life's second cycle of transiting Saturn aspects will be easier simply because you've learned from the first cycle represented by the time period from birth to the first Saturn return. Been there, done that.
As far as Jupiter and Pluto are concerned, I think you're right, other factors can certainly attenuate if there is some kind of reasonable orb of influence. Viewing Saturn in a vacuum, there appears to be a cyclical way in which the various transiting aspects to a natal point evolve, when viewed for simplicity's sake, absent apparent retrograde motion, and when limiting that view to hard, ninety degree angles, conjunction to square to opposition, followed by a symmetrical return to conjunction by passing first through the final square: then Saturn can seem overwhelming in the literature. This last square before return to conjunction is preceded by a Saturn trine Saturn, which sequential order is reversed in the other hemispheric division or symmetrical mirror image. This becomes a way to conceive that the last square before return might be easier than the first square afterward.
Another "seven" observation: this square, prior to the second return, is the 7th set of 90-degree points transiting Saturn makes to natal Saturn, the 8th would be your second Saturn return. Feelin' the Twilight Zone yet?
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