I am convinced that a rapture happens in the Spring for 2 main reasons. First, the Song of Solomon makes it clear:

My beloved spake, and said unto me, Rise up, my love, my fair one, and come away. For, lo, the winter is past, the rain is over and gone; The flowers appear on the earth; the time of the singing of birds is come, and the voice of the turtle (literally, turtledove) is heard in our land; The fig tree putteth forth her green figs, and the vines with the tender grape give a good smell. Arise, my love, my fair one, and come away.

Second, as Christ is the first of the firstfruits and the head of the body, that implies that there are remaining "firstfruits" which would be the bride, the Body of Christ. The barley harvest takes place in late Spring and barley is harvested by a winnowing fan after being thrown in the air--no "tribulum" is used as it is with wHEAT, or those harvested during the tribulation. And then comes the grape harvest, similar to "grapes of wrath" where they are literally crushed in the harvest.

Rarely do I see anyone mention Second Passover, which takes place 30 days after traditional Passover. It could "fit" according to what the article below states (Article from chabad.org):

A year after the Exodus, G‑d instructed the people of Israel to bring the Passover offering on the afternoon of the fourteenth of Nissan, and to eat it that evening, roasted over the fire, together with matzah and bitter herbs (they were not to break its bones--aka Jesus' legs not being broken on the cross), as they had done the previous year just before they left Egypt. “There were, however, certain persons who had become ritually impure through contact with a dead body, and could not, therefore, prepare the Passover offering on that day. They approached Moses and Aaron . . . and they said: ‘. . . Why should we be deprived, and not be able to present G‑d’s offering in its time, amongst the children of Israel?’” (Numbers 9:6–7).

In response to their plea, G‑d established the 14th of Iyar as a “Second Passover” (Pesach Sheni) for anyone who was unable to bring the offering on its appointed time in the previous month. The day thus represents the “second chance” achieved by teshuvah, the power of repentance and “return.” In the words of Rabbi Yosef Yitzchak of Lubavitch, “The Second Passover means that it’s never a ‘lost case.’” It is customary to mark this day by eating matzah, shmurah matzah if possible.

It was also for anyone who was "on a far journey".

So that comes up on Iyar 14 which is May 14th this year (May 15th is Israel's 66th bday).

Another potential for the rapture could be the 2nd month and 17th day--Jesus is coming "as in the days of Noah" and 2nd Passover technically falls on the 2nd month 14th day. I believe Noah entered the ark or was warned to load the ark one week before which would have been that very familiar scripture period of 40 days, marked from the beginning of the year. The "waters of the deep" breaking up and the deluge of rain happened on the 47th day. Additionally, torahcalendar.org stated that this is year 6,000 of the age similar to the fact that Noah was 600 years old at the time of the flood.

The third possibility that I rarely see mentioned is Lag B'Omer which takes place during the 50 day count leading up to Pentecost (from jewishweddingnetwork.com):

Because today, on Lag B’Omer, it is the 1st opportunity in a month to wed, many couples take advantage of the happy and spiritual nature of the day by choosing it as their wedding day. Since marriage is a time of utmost happiness for a couple, why not choose a day that symbolizes great happiness for the Jewish people as well?

Just some possible watch dates that could make sense coming up in the next 10 days or so.

Steve M