The following is from Kol HaTor chapter 1, page 33.
Little By Little:
To know ahead of time that the Atchalta DiGeulah comes little by little, according to Chaza"l (Yerushalmi Brachot): Thus is the Geulah of Israel, it comes little by little, like Ayelet HaShachar, "though I sit in the dark, Hashem is my light", and it continues until the day.
Thus it is with every action of the Atchalta, we should start with a little according to the verse "1 from a city and 2 from a family". It is an important rule according to the GR"A that all the things that in the future will be completed with the Geulah start little by little even in the Atchalta, thus in the building of Yerushalayim, we should start even from one stone. According to the verse "behold I have set in Tzion a foundation stone, a tried stone". For this stone is for a test to prove that it is the Will to build Yerushalayim and to expand the place of her tents, and Hashem will help us. Also in the secret of "and I will go slow".
We once asked our rabbi why does the Atchalta need to come davka slowly. If the desired time has come before Hashem to gather the dispersed of Israel, will the Hand of Hashem become shortened? That Kibbutz Galuyot should be the most part at one time?
Our rabbi explained to us that the entire matter of the Atchalta DiGeulah is when we are not meritorious. That is without the merit of our righteousness. And if the Geulah would come at once, behold from one side we would not be able to stand up to the measure of suffering that comes with Midat HaDin as mentioned above. And from the other side it wouldn't be possible to receive the great light that comes from the side of Chesed at once. All this it is imperitive for us to understand from the beginning on the way to the actual work of Kibbutz Galuyot.
What we can learn from this is as follows: We most certainly believe that if the level of Teshuvah done by Am Yisrael is sufficient, Geulah will happen in a pleasant and quick fashion. However, if we have not done Teshuvah by the time of the Keitz, the suffering, G-d forbid, would be great. Why would the suffering be so great?
Imagine the 999 Steps of Moshiach as a graph. The X axis is time, the Y axis is Am Yisrael's advancement through the Footsteps of Moshiach. The final Keitz, the latest point of X, is at the Y of 1000. Our desire is by our own actions to be at 999 when that day arrives. The further away we are, the more suffering, G-d forbid. The suffering is in direct relation to the steepness of the jump to 1000. If we are at 999, there is no suffering, akin to why we need not count the 50th day of the Omer. Just as we have done 49 days and kivyachol Hashem completes it, so too here, we arrive at 999 and Hashem completes the 1000.
The Keitz Meguleh means staying keeping up with the ascending line to perfection.
May Hashem help us to fulfill the tasks He has put upon us all.