Why does it say "b'Ma'alo Asher Ma'al"?
'Rashi': He transgressed twice - asking after Shmuel, and asking via a Ba'alas Ov 1 .
Vilna Gaon: Refer to 10:13:3:2.
Vilna Gaon: "Sho'el Ov" (Devarim 18:11) forbids asking to conjure up a Mes, and "Doresh El ha'Mesim" (ibid.) forbids asking matters from a Mes.
What is the meaning of "Asher Lo Shamar"?
'Rashi', Radak, Vilna Gaon: It was the matter of Amalek (Midrash Shmuel 24:7 - he did not kill Agag). 'Rashi' - also, he did not wait seven days for Shmuel (Shmuel I, 10:8, 13:12).
For how many transgressions did Sha'ul die?
'Rashi', citing Midrash Shmuel 24:7: He transgressed five matters - (a) he did not wait seven days for Shmuel; (b) he did not kill Agag; (c) he killed Nov, Ir ha'Kohanim; (d) he asked via an Ov; (e) he told the Kohen to desist (from asking from the Urim v'Tumim - Shmuel I, 14:19).
Vilna Gaon: There were six. "B'Ma'alo" is not waiting for Shmuel. "Asher Ma'al" is when he saw the masses going away, he told the Kohen to desist (from asking from the Urim v'Tumim). "Asher Lo Shamar" is [not killing the king and animals of] Amalek. "Lish'ol b'Ov Lidrosh" is two - conjuring via an Ov, and asking from a Mes (refer to 10:13:1:1*). "V'Lo Darash" (verse 14) is accepting Leshon ha'Ra about Nov 1 .
