We've seen this Sign means the following:
The "Wallets" of Charity Institutions are depleted as donations go to ("Jewish" but) non-Torah institutions.
Personal wallets are also depleted, as people spend everything, with all surplus going Charity (that would also help rectify the negative aspect of this Sign, relating to Charity Institutions).
But you're still spending money that you have.
Spending everything is extreme.
The following may be obvious but for the avoidance of doubt:
SPENDING MUST BE RESPONSIBLE AT ALL TIMES, SO AS NOT TO MAKE THE PERSON SPENDING NEEDY HIMSELF. HOW DOES THAT WORK? SPEND RELATIVE TO A STABLE SOURCE OF INCOME AND MARKETABLE GOODS/SKILLS, AS OPPOSED TO RELYING ON COMPLETE MIRACLES. CONSULT YOUR RABBI IF UNSURE.
Here's another meaning of this sign:
People have no cash –
But they're still giving to Charity.
That is, Moshiach will only come when people give to charity even when they have no available funds whatsoever.
How can that be possible?
I n t r o d u c i n g
It has now become normal to use:
Credit Cards for all purchasing (even if not in need of the credit)
Credit management techniques (such as Balance Transfers) to manage tight cash-flows. Borrowing to pay back.
Home Loans, and sometimes this is not even for paying back (interest only).
People can essentially spend even if their bank account is completely empty.
Easily and commonly done.
Extra-ordinarily ambitious – to give away funds that you don't even have. What a merit to bring Moshiach (itself extra-ordinary)!
Specifically makes the Redemption happen.
Out of No-Where
Giving Charity means we do an act of material kindness to others.
G-d then reciprocates kindness to the World (= “others” for Him).
The extent of Divine Kindness is proportional to the extent of our kindness:
Moshiach is all about revealing the infinity which is beyond the finite world.
And the above three extents of Charity all enable this monumental goal, one to a greater extent than the other.
NOTES & REFERENCES
Responsible spending even though donating more than 20% of income to Charity: Sefer Ahavat Chessed (Chafetz Chaim), Ch. 20.
Giving to charity even until, or even if when, there’s nothing in the wallet: That's the simple implication of Tanya Pt. 4 Ch. 10 at the end.
The extend of Divine Kindness mirrors the extent of our kindness: Based on the principle of "Measure for measure"