ὡραῖος re-etymologised seems plausible to me

[ἑκηβόλος]

Fitting ὡραῖος' sense of "beautiful" into a single etymological sequence, about "timely"-ness seems cumbersome.

Since ὁράω was a common everyday verb, I find it conceivable that ὡραῖος was re-etymologised in the popular imagination to mean "having the quality that we like to look at", "worth looking at", "beautiful", rather than ignoring the similarity and imagining that speakers in the post-classical period just extended the meaning of "youthful" to its connotation of "beautiful" - which extension in itself is quite pausible in itself, if however ὡραῖος did not sound so similar to forms like ὥρων / (ἑ)ὥρακα.

[Paul Derouda]

I think it must be an agricultural metaphor originally. A fruit ripe for picking is ωραιος, and similarly a person in the prime of their life. I don’t think οραω ever entered the picture.

The difference is that while in English ripe and mature are euphemisms for old, Greek ωραιος means ”just the right age”.

[ἑκηβόλος]

Okay. So it is a quality that pleases more of the senses than just sight.

Modern Greek only understands the sense of "beautiful", "pleasing to the senses", "nice" to ὡραῖος, and the New Testament and LXX examples, only use it in that sense of pleasing to one or other of the senses too. Ie. those other broad range of time-related meanings were lost at some point.

If the other meanings of ὡραῖος don't continue past a certain point in the popular language, but were replaced by this new "pleasing to the senses" meaning, there are a a couple of ways to think about that. First, if it is an evolutionary bottle-neck in the word's development, where the connotation meaning "pleasing to the senses" is all that is left of the word's use, replacing the formerly dominant "seasonable" in the lexical semantic ecology of the language - the lovely smell of fruit in the pantry and after-taste of fruit in the mouth, then there doesn't need to be much association between a farmer's agruculture experience of the growing of fruit and its seasonable ripening on the one hand, and an urbanite's somewhat detached experience of fruit as a well-pleasing experience of the senses. A detachment from the agricultural experience, through the economic development of horticulture (orchards) and commerce, could have been what triggered some form of synæsthetic lexical semantic evolution radiation event whereby other forms of sensory pleasing are possible too - things like sound are mentioned in the Song of Songs among others. If, on the other hand, it remained tied to the agricultural experience, perhaps the meaning widened due to some genius of bucolic romanticism affording a good balance in the humours.

Another related question...

I'm not familiar with the abbreviations for all these authours... Are the range of authours quoted in this part of the LSJ entry all post-classical too? -

b. generally, beauty, grace, elegance of style, D.H.Pomp.2, Plu.2.874b, etc.; “γλυκύτης καὶ ὥ.” Hermog.Id.2.3, cf. Men.Rh.p.335 S., Him.Or.1.2; of beauty in general, “χάρις καὶ ὥρα” Plu.2.128d.

[ἑκηβόλος]

Etymology was probably an inappropriate peg to hang my thoughts on initially with this ... but anyway, ...