Thank you for posting the copies. Well, the ENTIRE context of the discussion is 1) in the event that a woman notice that a particular man might be tempted to sin by her dress (and St. Alphonsus, for the most part, lumps makeup in with dress) or 2) in the event that a woman believes that it might generally be a temptation to sin to men. And then the context is always if the intent is out of vanity. And finally the context of the makeup issue is on account of men not wanting to be deceived. Women can be justified in some extravagence of dress if allowed by men (their husbands in particular) but St. Alphonsus says that makeup is always a sin based on the assumption that no man would want to be deceived. So that is the rationale he gives.
Also, the "it's always a sin" is not a direct quote from anything I've ever seen from St. Thomas.
Throughout the entire discussion, the three key factors are 1) motivation (active incitement to lust, indifference about inciting to lust, vanity, custom, etc.); 2) effect (does it tempt to sinful lust either a particular individual or a class of individuals); 3) whether it's by permission from their husbands (or otherwise approved of or tolerated by men in general).
There is NO ABSOLUTE STATEMENT being made anywhere to indicate that the wearing of makeup is intrinsically evil regardless of the motivation behind it and its effect.
I agree with some of what you say, but a few clarifications:
1) The context is given by the Chapter heading (See Pic #3), which is "passive scandal," which means for the most part, we are discussing women leading men into sin without intending to (i.e., passive), and the discussion is therefore mostly regarding the level of culpability in such cases;
2) It is not St. Alphonsus's rationale that makeup is always a sin, and that no man would want to be deceived, but St. Thomas's (see bottom pargraph in Pic 5, p. 582).
3) The "it's always a sin" most certainly IS a direct quote from St. Thomas (Commentary on the First Epistle of Timothy, Ch. 2).
4) Regarding my observations in 2 & 3 above: My guess is that you missed the quotation marks where Alphonsus transitions from his own commentary to the direct quotation of St. Thomas, which is easy enough to do.
5) I do not dispute the "three key factors" you identify, which are all natural enough, since the article regards passive scandal, and these three are evaluated to determine the level of culpability. But what I do not see anywhere in the excerpts provided is anything permitting makeup at a level less than venial. The discussion only vacillates between venial and mortal, but never is an explicit permission for makeup given for any reason period.
6) Finally, regarding your final statement that "there is no absolute statement being made anywhere to indicate that the wearing of makeup is intrinsically evil regardless of the motivation behind it and its effect:
The only context I can come up with which would limit or constrain the absolute statement "makeup is always a sin" is that he is referring to makeup in connection with feminine vanity. Consequently, I suppose you could make an argument it is permitted on stage, or for charity (e.g., St. Thomas gives the example of hiding a disfigurement, which I take to be something more than acne and rashes, or it would still be vain rather than charity, but whatever), etc.
But that doesn't really get the makeup advocates anywhere, because they have stated their perception of a need to use makeup to catch a man (i.e., vanity = sin).
At this point, though I am disposed to continue hearing other possible alternatives, I believe that St. Thomas and St. Alphonsus's distinction between attire (exceptions) vs makeup (no exceptions, except possibly along tho order of those just mentioned above) provides the true position, and reconciles/harmonizes what at first seemed like a contradiction in St. Thomas between his writing in Q169 vs Commentary on First Epistle of Timothy.
Which is all to say I think that vanity is intrinsically evil (i.e., always a sin), and that if cosmetics can be worn for motives not involving vanity, go for it.
But nearly every plea in this thread (need it to get a man; need it to feel good about self; want to look good for the other women; etc) has been based on vanity.
In such cases, I think St. Thomas's "makeup is always sinful" surely applies.