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Iliad XXII.307:
τό οἱ ὑπὸ λαπάρην τέτατο μέγα τε στιβαρόν τε
Since it's at the beginning of a hexameter, τό needs to scan heavy. And since omicron is always short by nature, it must be heavy by position.
But how can οἱ make position? Etymologically, my understanding is that it comes from *so-, which still has only a single initial consonant. Is my logic wrong? Or is there some special convention I've missed?
The dative οἱ, like the other singular inflected forms of this pronoun (acc. ἑ, gen. οὑ), is thought to come not from the PIE demonstrative *so- but from the reflexive *swe, a PIE accusative form which apparently served as the basis for the innovated Greek dative and genitive. I'm away from my reference books at the moment, but the Wiktionary page gives some more information. The initial cluster *sw- is presumably the reason why this and the other case forms of the pronoun often make position, though by the time of the Homeric poems it was presumably no longer [sw] but [hw] or perhaps [w:].
τό οἱ ὑπὸ λαπάρην τέτατο μέγα τε στιβαρόν τε
Since it's at the beginning of a hexameter, τό needs to scan heavy. And since omicron is always short by nature, it must be heavy by position.
There are actually more than two possibilities, since there are several cases in which a short syllable is treated as long even when it does not make position.
In this particular case, I think there are two possible answers. First, Allen Rogers Benner says:
I personally think this is not the likely reason in this case, because the examples cited are all two-syllable words that frequently need clause and sentence initial position for syntactical reasons. Banning such words from beginning verses would cramp a poet's style. The pronoun τό, however, is not clearly needed in clause/sentence initial position.
The second possible answer has two parts, which Allen Rogers Benner describes this way:
A short final vowel may make a long syllable when the next word begins with a liquid λ, μ, ν, ρ—or digamma, or sigma. E. g. A 233.
In many instances where a short syllable seems to be used for a long, closer examination shows that it is really long by position. The value of a consonant (especially digamma) often remains, even when the letter itself has disappeared from the text. E. g. A 416. So too 3.2, 230, etc. Whether the initial consonant of “ὡς”, ‘like,’ was “ϝ” or y is uncertain. At any rate, it had disappeared in the Homeric age; its value was retained, however, in formulas like the one quoted, which were inherited from older time.
Allen Rogers Bennet, in his notes to the Iliad, cites this last explanation for the line in question. Apparently οἱ descends from Proto-Indo-European *yós, which would have yielded an initial "y" (/j/) in proto-Greek and perhaps down into the time this poetic formula was first devised. Since "y" (/j/) has phonetic features similar to digamma, it apparently could be doubled after a short vowel according the first rule above, making the short vowel long by position as you surmised.
If this doubling of liquids, sigma, digamma and "y" (/j/) is indeed the explanation, it is notable that this verse unusually contains three instances of such doubling, with the initial original consonants of: οἱ, λαπάρην, and μέγα.
