What is the significance of the fact that the Cloud rose from the Mishkan ha'Eidus on the twentieth of Iyar?
Rashi: It teaches us that they encamped in front of Har Sinai ten days short of a year. 1
Seforno: It teaches us that no sooner were the trumpets made - immediately following the Korban Pesach Sheini, than they were used to announce Yisrael's departure from Har Sinai.
Oznayim la'Torsh (according to Kabalah: Because the Cloud did not rise from the Camp as long as the Simchah of Pesach was present - and the Crown (the Simchah) of Pesach remained thirty days after Pesach. 2
When the Cloud rose from the Mishkan ha'Eidus, where was it about to lead them?
Rashi and Seforno: It was about to lead them to Kadeish Barne'a 1 (the first town that they would encounter on the border of Eretz Cana'an - Seforno) from where they were destined to enter Eretz Yisrael and begin the conquest of Cana'an. 2
A journey that should have taken eleven days, but which took them only three (See Rashi in Devarim, 1:2)..
Seforno: See Devarim, 1:19, and Rashi there on Pasuk 29.