Well, that's a lot to cover!
To me, Elul really starts with Shabbos Chazon. While the Haftara warns of the imminent destruction of the Bais HaMikdash, it also exhorts us to do Teshuva, because it's never too late. And of course, the Haftara of this Shabbos has the famous possuk we say many, many times during the Teshuva Season:
Go forth, now, let us reason together, says Hashem. if your sins are like scarlet, they will whiten like snow, if they have reddened like crimson, they will become [white as] wool.
The Shabbos, we begin to read the seven Haftarot of consolation, the "Shiv'a D'Nechemta." These Haftarot are replete with prophesies of the future, when Hashem no longer turns His back on Yerushalayim and the Jewish people, when the Jewish people truly return to Hashem, and when Hashem finally grants us a Geula Shleima. They culminated last Shabbos with the last of them, and the last possuk tells us:
In all their troubles, He was troubled,and an angel from before Him saved them; with His love and with His compassion He redeemed them; He lifted them and bore them all the days of the world.
These Haftarot never fail to make me cry, and I've never understood anyone who doesn't when they read them.
We then have the minhag to say Selichos, beginning, most years, on the Motzei Shabbos before Rosh Hashana. Selichos is something with which I've an issue. There are so many of them, and they are so long, that by the time I get to Rosh Hashana and Yom Kippur, I'm so sick of it I have no emotions left for when they really count. So, mostly, while I mentally ready myself for the Yamim Noraim, I don't usually say Selichos at all. I have a feeling they exist simply to make happy the poets who composed them. They didn't make the Rosh Hashana/Yom Kippur cut, so we has to do something with them, right? :)
Does this make me less frum? I don't think so. For some people, Selichos are necessary. They prepare a person for the Yamim Noraim. For some, like myself, they are simply too long and, quite honestly, meaningless. It's interesting to note: While I was in Yeshiva, and later davening in a Yeshivish shul, they skipped many of the Selichos anyway. I'm not saying not to say Selichos. But it is a minhag, not Halacha, and if saying Selichos is detrimental to one's quality of davening on Rosh Hashana and Yom Kippur, why say them? We're taught, while learning Torah, that quality takes precedence over quality. Why not the same with davening? Remember, God doesn't just want someone mumbling a bunch of stuff, and the more the better. God wants people to repent and Return to Him. That's the point of Rosh Hashana and Yom Kippur.
More later! If I don't write before Rosh Hashana, I would like to wish all my readers a wonderful new year of bracha, hatzlacha, peace, and all the best.
Shana Tova U'Metuka.
Am Kshe Oref