That "Philo didn't read Hebrew" is definitely not true. It is certain that Greek was his first language, but that "didn't read Hebrew" is certainly not true. Even if it were true, it only weakens your position, since it just shows that the translation of 'qanah' as 'ktáomai' was a well-known and established Jewish reading back then, since all Jewish translators and interpreters after the LXX rendered it this way. And Jerome did not invent it himself, but while learning Hebrew from the Jews in Bethlehem took this reading from them, which was unknown before among the Greek and Latin speaking Christians, who had to defend the "begotten, not made" principle of the Son based on translation using the verb "ktizo" from the LXX. Check this: http://www.myriobiblos.gr/texts/english/christou_crebegot.html
"As it is, “acquired” is arguably closer in meaning to “created” than Jerome’s “possessed”"
Wrong, these these ancient Jewish translators and interpreters did not translate קנני (qānānî) with the English word "acquired", but with the Greek word ἐκτήσατο, which is third-person singular aorist middle indicative of κτάομαι (ktáomai), which has the following meanings:
κτᾰ́ομαι • (ktáomai)- (transitive) to get, obtain, acquire, gain, win
- (transitive, of consequences) to bring on oneself, incur
- (transitive, perfect and pluperfect) to have acquired, have, own, possess
" in the crucial sense that an acquisition is a point in time, whereas possession is a state of affairs."
Here we are not talking about any kind of "temporal" happening in specific "a point in time", but rather a poetic speech, from which it is hardly possible to derive a doctrinal principle.
"The accompanying “first of his works” and “founded me” also point toward God creating wisdom before anything else."
There is no such thing as "first of his works" or "founded me" in the text. Instead, "at/as the beginning of his ways" and in thext verse "I was set up from everlasting, from the beginning, or ever the earth was." is in the text. The meaning of נָסַך (nasak) is not "founded me," but "anointed" (compare Psalm 2:6), "to pour forth" (as of molten metal), then "to put down," "to appoint or establish." In the Septuagint, "he established (ἐθεμελίωσε) me;" Vulgate, ordinate sum; Aquila, κατεστάθην; Symmachus, προεχείρισμαι; Venetian, κέχυμαι. There is no "timeliness" involved. So what is said here is that Wisdom was from everlasting exalted as ruler and disposer of all things. To express eternal relationship, three synonymous terms are used. From eternal; πρὸ τοῦ αἰῶνος, Septuagint, as Delitzsch notes, points back to infinite distance. Especially since the next phrase marks this "nasak" as "from the beginning". Compare 'rosh' in Exodus 12:2, Numbers 10:10, 28:11, Judges 7:19.
"JWs agree that the creation of Jesus was different than the rest of creation because Jehovah created Jesus directly whereas he created everything else through his Son."
However, that is not a significant difference, especially since, as it cannot be emphasized enough, the New Testament emphatically describes the Son's orign from the Father exclusively with the verb "begotten" (gennao) or "born" (tikto), which the New Testament never uses for the created world. So why can't the one used by the New Testament be accepted?
"The point of the quote from Origen was to show that he held a similar view about God first creating his Son"
Wrong: even if he used the term "ktizo", you cannot use it in the Arian/JW sense (which is practically: poio), because it turns out that Oirgen did not interpret it that way, so his citation is out of context, also disregarding nuances lost in translation, so it is unfair to the author. Dionysius of Rome pointed out that "there is more than one meaning of the word created" (ktizo), and "this created is not to be understood in the same manner as made". You would have the burden of proving that Origen did not mean it that way. Check: De Principiis IV.27, I.6, II.2.2, II.4.3, etc., also: