What is the meaning of "u'mi'Bamos ha'Gai ... "?
Ramban, Targum Onkelos and Targum Yonasan: 'From the desert the well went with them down to the valleys and from the valleys to the high places'.
Rashbam: 'Matanah', 'Nachaliel' and 'Bamos' are all place-names.
Seforno: The Pasuk implies that in spite of flowing with them to all of these places, the well lost none of its water along the way - an additional facet of its supernatural qualities.
Refer to 21:19:1:2 & 8.
What is the meaning "Rosh ha'Pisgah ve'Nishkafah Al P'nei ha'Yeshimon"?
Rashi #1: It means 'to the top of the cliff 1 that overlooked Yeshimon (a desplate place from the word ?Shemamah?). 2
Rashi #2 (citing Midrash Tanchuma): With reference to the well, which was buried (after Moshe died) in the Sea of Teverya (the Kineret), 3 the Pasuk means that, if someone stands on the cliff of Yeshimon 4 and looks down into the sea, he will see something that resembles a sieve - which in fact, is the well of Miriam. 5
Rashbam: Refer to 21:18:4:2.
Why did the well stop accompanying them specifically at that spot?
Rashi: Because that is where Moshe died. 1
Targum Yonasan: Because they were lax in the Mitzvah of Torah-study.
Oznayim la'Torah (in Pasuk 16): Becsuse they now had many streans of water from which to draw.
Sifsei Chachamim: Because, even though it ceased after the death of Miriam, it returned on the merit of Moshe. See also Ba?al ha?Turim.