Where should the Messianic application begin and end in Jacob's blessing to Judah?

Question

In Jacob' blessing to Judah (Genesis 49:9-12) both ancient Rabbinic and ancient Christian commentators have assigned the Messiah to be 'him' (in Hebrew 'Shiloh'). However, starting at 'Binding his foal to the vine' several Christian commentators say it no longer applies to the Messiah, even though ancient rabbinic and early Christian fathers still carry the words in respect to the Messiah.

My question is where should the words be interpreted as principally meaning the Messiah and where should they stop and simply mean the literal Judah?

For example, with regard to the pre-Christian era, the whole section is treated to be as Messianic according to some ancient rabbinic literature:

The expression ‘lion’s whelp,’ is explained of the Messiah in Yalkut 160 (vol. 1. p. 49 c), no less than five times; while the term ‘he couched,’ is referred to the Messiah in Ber. R. 98....Jerusalem Targum, as well as Sanh. 98 b, the Midrash on the passage, and that on Prov. 19:21, and on Lam. 1:16, where it is rendered shelo, ‘whose it is,’ refer the expression ‘Shiloh,’ and, indeed, the whole passage, to the Messiah; the Midrash Ber. R. (99, ed. Warsh. p. 178 b) with special reference to Is. 11:10, while the promise with reference to the ass’s colt is brought into connection with Zech. 9:9 ('The Life and Times of Jesus the Messiah', by Alfred Edersheim, Appendix 9)

For example, under the Christian era, Luther thinks similar to many church fathers that Shiloh will bring so much spiritual blessing that even an ass will be drunk on abundance:

Nor is an ass usually tied to a vine to carry the grapes, but this is done in order that the ass may drink and be filled with wine. Therefore the words seem to have the following meaning: The ass is to feed on grapes and wine as nourishment and to get drunk. The ass shall have good days for once and guzzle wine. (Luther's Works, Vol 8, Page 2427)

However Calvin and many other conservative commentators take the mention of wine and milk as simply hyperboles for Judah's literal prosperity in Canaan and so end the direct application to the Messiah earlier.

Here are the Bible verses in question:

Judah is a lion 's cub; from the prey, my son, you have gone up. He stooped down; he crouched as a lion and as a lioness; who dares rouse him? The scepter shall not depart from Judah, nor the ruler's staff from between his feet, until tribute comes to him; and to him shall be the obedience of the peoples. Binding his foal to the vine and his donkey' s colt to the choice vine, he has washed his garments in wine and his vesture in the blood of grapes. His eyes are darker than wine, and his teeth whiter than milk. (Genesis 49:9-12, ESV)

Answer 1

The verses in question in condensed form say:

a) Judah is like a lion.

b) Judah will keep the scepter until someone comes (Shiloh) who will receive the obedience of other nations (or bring rest to the nations).

c) Judah will enjoy great prosperity

I have not encountered a Christian commentary that did not accept b) as indicating that the kingdom of Judah will literally retain a kind of kingdom until Christ came. Although I am sure some may exists that fact that they are hide to find pretty much leaves the debate on a) and c)

The question is really whether to include a) and c) as referring to Messiah while also referring literally to Judah. What makes this more difficult is that b) literally refers to Messiah and is not just a deeper aspect of the literal, therefore one can just take a literal read of a) and c) and have the subject Messianic without a deeper meaning from the hyperboles in c) or the symbolic origins of the rise in a).

However, this temptation to limit Messiah to b) does not seem something that should be strictly enforced for the rising of Judah is arguably in itself is a type of the rising of Christ. The literal rising of Judah in order to preserve a lineage that a Messiah could be born through the seed of David, until Messiah comes and obtains the obedience of the nations, must in of itself indicate the rising of Messiah, for the whole tree is grown for the purpose of its fruit. The whole glory that it obtains is for the fulfillment of its final reaching end. Therefore, it is better to understand that the whole blessing encompasses a Messianic expectation. That from a small cub, destined to strength, would come a strong people, who would continue and in Christ take over the whole world in untold spiritual wealth. The plain literal achievements of Israel, peaking at David and Solomon, never came close to following the grand images of this blessing to Jacob.

One thing I have become convinced of about Messianic prophecies is that one can't be to confident about where they begin and end. I believe the lack of confidence is necessary for the subject as Messianic prophecies are like shadows of a future reality. Shadows by nature have unclear edges and gradients of uncertainty while yet clearly casting a general image. Sometimes the ideas in hyperbole seem to flutter slowly away from a literal train of thought, reaching crescendo, and then smoothly falling back into less exaggerated speech. Like I see this case. At other times it seems more abrupt, in both the start and the ending points. Calvin took and abrupt 'only in b)' stance along with other modern commentators such as C.F. KEIL and F. DELITZSCH, who I am growing to appreciate more and more. Like I said in the question, Luther, for example, like early church Fathers took an approach like my own thoughts.