Choices - Questions on Kismet

When do you make the choice of how much of a card's effect to activate, in general?  Less generally, the situation I'm currently looking at is Vicious Cyclone played on Kismet with Inconceivable Obstruction in play.  Do you choose to discard 1-3 cards, then deal 1-3 damage instances, the first of which possibly produces a new Environment Target?  Or can you discard one card, trigger the Obstruction and see what happens, and then proceed with discarding 0-2 more cards, depending on whether you'd rather play them based on the Obstruction's outcome?

Since it says "At the start of your turn, discard up to 3 cards. Tempest deals that target 1 projectile damage for each card discarded this way" First you'll do the first sentence, after making your choice you will carry on to the second sentence. Now you are passed the first sentnece, so no turning back now.

Welp, I pretty definitely didn't win that game.  Fairly sure I screwed up the rules and should have died sooner, but even best-case scenario, I was at 10 HP and about to be hit for 1+5 jinxes in play damage, then possibly damaged again by one of two cards Kismet can play in a turn if the second one's Lucky.  Very hard for a single surviving hero to get the talisman flipped in a turn AND make any headway against Kizzy, especially with both Obstruction and Lady Luck in play.

While I'm asking questions about the Kissy One, another thought occurred to me.  This fight took place in the Realm of Discord, and at one point, for a brief moment, Imbued Vitality was in play, and I was very excited about the prospect of being able to beat up IO so it would stop keeping me from beating up on Kismet.  Alas, Imminent Destruction nuked the Vitality, so it was not to be.  Lady Luck wasn't in play at the time, but I find myself wondering what would happen if it was?  Once IO (or any other villain card, even Lady Luck itself) is reduced to 0 HP, it should be destroyed for that reason - but Lady Luck tries to prevent that destruction by finding a non-Lucky card on Kismet's deck.  Assuming this occurs, does that mean IO is immediately destroyed again, triggering Lady Luck again, and this cycle keeps going until Kizzy gets a Lucky card (or, assuming none are left in her deck, until every card left has been revealed and discarded, making the final reveal impossible and thus allowing the destruction to finally occur)?

This is how I personally would handle it.

I agree.