Welcome back! Long time no write, but that's what happens when there is too much going on. A few thoughts to close out Pesach:
1. The Chasam Sofer in his derashos is mechadesh that when the ultimate geulah comes we will still have to celebrate a yom tov sheni shel galiyos as a remembrance of the days of galus in which we now find ourselves. He compares this to the renaming of the months of the year post-galus Bavel from chodesh ha'rishon, chodesh ha'sheni, etc. to the names we now have as a way to create a remembrance of the years we spent in Babylonian exile (see Ramban, Shmos 12). Interesting... Seems to me that one can distinguish between the two ideas. Yom tov sheni is not a function of galus per se, but is a function of living too far from Eretz Yisrael to receive prompt calendar updates from messengers of Beis Din and therefore having a safeik as to when to celebrate Yom Tov. Even b'zman habayis, yom tov sheni would be celebrated by those outside Eretz Yisrael.
2. My wife gets the credit for pointing out an amazing Sefas Emes (5642 d"h b'Shir haShirim) that explains that just as our ancestors were 100% convinced that the galus in Mitzrayim would go on for 400 years and never imagined that Hashem would hasten redemption by counting the qualitative intensity of servitude as a substitute for the quantity of years required, so too, we are all convinced based on our mesorah and seforim that the tzaros of chevlei moshiach will be painful and tragic, but it could be that the length of our galus, the quantity of time we have spent in exile, will serve as a substitute for the intense quality of pain predicted. The galus may be long, but this may be b'chasdei Hashem a means of ultimately lessening our overall pain.
Sefas Emes goes on to say (based on Midrashim) that the whole machlokes (Shabbos 55a) whether the merit of zechus Avos still can be invoked is irrelevant to our achieving geulah, as even if we have exhausted our zechus Avos, there is a far deeper well of rachmanus we can draw on in the form of zechus Imahos. It is in their merit that the future redemption will come.
3. We use besamim for havdalah on motzei Shabbos because we need some cheering up after the neshoma yeseirah, the extra neshoma spark we have on Shabbos, departs. Why then don't we usually use besamim for havdalah on motzei Yom Tov as well (motzei Yom Tov that coincides with motzei Shabbos, like this year, is an exception)? The usual answer given is that on Yom Tov we don't have a neshoma yeseirah (see Tos. Beitzah 2b).
The Shem m'Shmuel (5672) quotes a different approach in the name of his father (based on a Ramban). He suggests that the kedusha of Shabbos is so intense and beyond us that the departure of Shabbos is like falling off a spiritual cliff -- we need some way to catch ourselves and adjust to the radical change. Not so Yom Tov. The kedusha of Yom Tov is something we can relate to; we feel the enjoyment and beauty of Yom Tov in a different way than we do Shabbos. There are no besamim in the havdalah of motzei Yom Tov not because we lack a neshoma yeseirah on Yom Tov, but rather because that neshoma yeseirah lingers with us and does not flee as we transition back into the days of chol.
So maybe that's not just yet-undigested matzah that you feel still sitting there inside... maybe it's really just a little bit of the neshoma yeseirah from Yom Tov still hanging on. No rush to let it go.