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Interpretation 2 is correct. The first time you make a roll that could be affected by Fortune, it kicks in (but, you don't have to use it on that roll).

I’m trying to understand the order of how this works. (this assumes only one round of fortune and no cackling)

1. Witch cast fortune on character
2. Character faces <insert relevant check here>
3. Character decides whether to use fortune or not
4. If so, roll twice, then skip to line 11
5. If not, roll once, then continue on
6. Character faces next <insert relevant check here>
7. Character decides whether to use fortune or not
8. If so, roll twice, then skip to line 11
9. If not, roll once, then continue on
10. Round ends
11. Fortune duration has ended and cannot be used again this day
Or
1. Witch cast fortune with soothsayer on character
2. Character does not face combat for 3 hours and soothsayer doesn’t kick off
3. Character now faces <insert relevant check here>
4. Soothsayer kicks off
5. Character decides whether to use fortune or not
6. If so, roll twice, then skip to line 13
7. If not, roll once, then continue on
8. Character faces next <insert relevant check here>
9. Character decides whether to use fortune or not
10. If so, roll twice, then skip to line 13
11. If not, roll once, then continue on
12. Round ends
13. Fortune duration has ended and cannot be used again this day

So, fortune with soothsayer is only useful for buffing up a group prior to a fight, then needs to be cackled to maintain it. The recipient doesn’t get the choice to use it when he needs it most? Their only option is to use it most effectively within the duration allowed? I’m not going to say it’s useless, but its versatility has been severely limited with that interpretation.

If I’m way off base here, please explain what I’m missing.

That was my understanding as well. If the player doesn’t invoke the fortune, then that check couldn’t be affected. Therefore, the player has the choice of when/where to use fortune. This fits within the boundaries dictated by both powers.

An argument has occurred on the interpretation of using a witch’s fortune hex with soothsayer hex.

Fortune states:

“The witch can grant a creature within 30 feet a bit of good luck for 1 round. The target can call upon this good luck once per round, allowing him to reroll any ability check, attack roll, saving throw, or skill check, taking the better result. He must decide to use this ability before the first roll is made. At 8th level and 16th level, the duration of this hex is extended by 1 round. Once a creature has benefited from the fortune hex, it cannot benefit from it again for 24 hours.”

Soothsayer states:

“When the witch uses the evil eye hex, fortune hex, misfortune hex, or retribution major hex, she can choose to delay the effect. If she does so, the hex takes effect the next time the target makes a roll that could be affected by the hex (such as an ability check, attack roll, saving throw, or skill check) or is affected by an action that could be modified by the hex (such as being attacked when the hex would affect the target's AC), whichever comes first (ignoring actions that are not in combat and actions that have no penalty for failure). The duration of the hex begins on the same round as the action that causes it to take effect. The hex is wasted if it is not triggered within 24 hours.”

Interpretation 1 says, witch cast fortune with soothsayer in the morning on the wizard. Later that day, the wizard attempts to cast a spell on a dragon and has to make an SR check. The wizard feels confident and rolls the check without fortune. Next round, the dragon unleashes its breath weapon. The same wizard is unsure of its reflex save and “calls upon his good luck” and uses fortune. Fortune has been activated that round and now its duration begins. The next morning, the witch uses fortune on the wizard again and the cycle continues.

Interpretation 2 says, same witch, wizard and routine. When facing the dragon’s SR check, this is “next time the target makes a roll that could be affected by the hex.” The wizard is required to use fortune on this check or lose its benefits. Next round comes the breath weapon and the wizard is without fortune to help his save. If the wizard survives, the next morning, fortune can be cast again.

The point is, does the recipient of a fortune with soothsayer get to decide when and where their fortune kicks off or is it just the next time a check is required?

Sorry for the long post, but any help would be appreciated.