Elijah said to Rav Y’huda the brother of Rav Sala the Pious: “The world will exist for no less than eighty-five jubilees [that is, 4250 years], and in the last jubilee the Son of David will come.” He asked him: “In its beginning or at its end?” He answered: “I do not know.” [Rav Y’huda then asked:] “Will it [the last jubilee] be complete or not?” He said to him: “I do not know.” Rav Ashi said; “This is what Elijah told him; ‘Until the last jubilee expect him not; from then on expect him.’” Babylonian Talmud Sanhedrin 97b[14]
From the above dialogue it appears we're meant to expect the Messiah to either come on the First Day of the Jubilee Year or on the Last Day of the Jubilee year.
I believe the confusion of not knowing whether the Lord would come on the first or last day of the Jubilee Year stems from the following verse:
"So you are to know and discern that from the issuing of a decree to restore and rebuild Jerusalem until Messiah the Prince there will be seven weeks [that is, 49 Years]..." [Dan.9:25]
The decree was issued on the 28th of June 1967, after which seven weeks of 49 Years of 360 Days each, expired on the 14th of October 2015. The above verse is telling us that after 49 Years of 360 Days, the Messiah the Prince will come for His Bride, the Remnant Church. We now know that the First Day of the Jubilee Year fell on the 15th of October 2015. And the Messiah the Prince certainly did not come on that Day! Which means we can watch with great anticipation for the Messiah the Prince to come for us no later than on the 8th of October 2016, which is the Last Day of the Jubilee Year. That Day is also the Great Day of the Feast of Tabernacles according to the Creator's Calendar!!!