Jewish Crises
Secular Education
Was that a bad thing?
Intellectual enlightenment -- the study of science, music and art -- is "Kosher" if done in the right way and for the right reasons.
During this period in History, studying Secular Education was the gateway to abandoning tradition and never looking back. The outcome speaks for itself -- over 80% of the young generation that were born in Jewish villages (Stetl) in Poland after 1880, discarded their Jewish observance, due to the Haskalah and Socialism.
Ironically, this very Enlightenment forms part of the Good Signs for the Coming of Moshiach (to be elaborated on in future topics, G-d willing). However it has also been the vehicle for these Unpleasant Signs...
All four signs have been
Fulfilled
in the above-mentioned events*
1. Informers will increase

Never in history* have we seen such organized Jewish forces like the Haskalah and Yevsektsia crystallize and act in alliance with the antisemitic authorities to destroy Judaism.
These were the "strong winds" that attempted to destroy the "Jewish Tree".
2. Scholars will decrease

With so many Jewish children drafted to the Russian Army, Jewish day schools taken over by the Haskalah, and then all Jewish schools closing down (in Russia), as well as two World Wars happening around the same time, Torah students and Torah learning hit a history-record low.
So the roots that keep the Jewish Tree alive have been significantly reduced, jeopardizing the future of the Tree, even with no winds, de-fertilization, and old age. How-much-more-so with them three.
3. Wallets will become empty of coins

Throughout history, Jews suffered economically as well.
But no matter how little funding was available, Torah institutions were supported. These kept the Jewish Tree alive.
With mass secularization, funds that were previously spent on Torah Institutions were sent to cultural and political "Jewish" institutions, which did not advance Jewish values and often acted against them.
Such institutions are like weeds around the Jewish Tree, exhausting the local nutrients, which not only stop the tree from growing but also jeopardize its existence.
The "Wallets" refer to the pools of funds (bank accounts) of the Torah Institutions* which were forced to close or at most really struggle to survive.

Jews always believed redemption from the troubles of Exile will come from G-d (and what we need to do is fix up our sins).*
The motive behind Zionism however is different: We have to take matters to our own hands to obtain salvation as it ain't coming from Above. Effectively this is giving up on the Redemption (and G-d) and devising alternative means to secure the future.
The Jewish Tree (hope for G-d's Redemption) has grown too old and is perishing as the masses veer toward Zionism and the State of Israel which have supposedly superseded it.
4. People will give up on the Redemption
Post WW2
The Signs haven't gone away
The impacts of the above signs are ongoing, as can be readily seen in the Post World War II Era.
Here are some:
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Assimilation keeps trending up
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Majority of Jews identify themselves as "Secular"
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Hatred of Judaism within Jewish camp
So according to these four signs, Moshiach is ready to come (and has been for a while now...)
Coming Up
We still need to understand:
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How is the Jewish "Tree" managing to survive these Signs??
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How these signs indicate the arrival of Moshiach? Seemingly there is no connection...
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Why does Moshiach's arrival depend on these signs?
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Why Moshiach hasn't come yet if these Signs have already happened?
REFERENCES AND NOTES
How all four signs have been fulfilled: See the book "Bet Hashoeva" pp 66-69. It then also becomes clearer how all these four signs are not isolated from each other, but are four different aspects of the same historical chain of events, starting with Enlightenment and ending with Zionism.
Never in history has there been such organized Jewish forces like the Haskalah and Yevsektsia to destroy Judaism: Well, the Hellenists came close. In the times when the Greek Empire was ruling over Israel, there formed a significant movement within the Jewish People to adopt the popular Greek culture. However, although affecting the highest levels within the Jewish Government (High Priest), there was no persecution of the people to adopt the new faith by the Hellenists. It was the attractive new culture that was endangering Jewish Tradition. Later on, when the Syrian Emperor Antiochus Epiphanes started using brutal force to suppress Judaism (the first religious persecution in history, eventuating in the victory of Chanuka) it was him and his Syrian soldiers who were the force behind it, not the Hellenists.
"Wallets" refer to the bank accounts of Torah Institutions: The Rashash's (Rabbi Shmuel Strashun of Vilna) commentary on Rashi's commentary on Talmud Sanhedrin 97a, based on the Mishnah's plain reference to wallet (כיס - "kis") as that of a Charity (see Ketubot 6:5). However he puts a positive spin on this to say people will be so rich that even the smaller donations will not consist of small coins (פרוטה - "pruta").
Redemption coming from G-d: See Deuteronomy 30:1-5 and many places throughout the Prophets. Regarding whether and how G-d's salvation depends on our repenting -- see Talmud Sanhedrin 97b, and Rambam Laws of Repentance 7:5. Jewish Tradition and Law are clear that our actions go only as far as arousing Salvation from Above (through Moshiach), not making the Redemption happen regardless and independent of the Almighty, Heaven forbid.