I really like what everyone has said.  Sil being used to message Lucy or Clarissa is genius.  It seems like Option 4 mixed with Clive going to the village of Cherrad is the idea forming, so far.  I like it.

To add to what others have said; I'd say Clive should take some gold to sponser the journeys of the prospective 'Cherrad messengers.'  The [i]closest[/i] city that could have reinforcements might not be too far for the one messenger.  Capitol City, however, might require a long trip - like, weeks maybe - that needs resources, so a gold piece or two, might go a long way for the other messenger to take up the big task.  

Also; if a message can be sent to Lucy or Clarissa and Second Chance's arrival can be expected, our characters can probably be successful as soon as midnight replenishes the magical abilities.  Coupled with Adam's ability to create cover, I don't think a distraction would be necessary from anyone except maybe Sil.  Our two Rangers should make this a breeze.  Fenna is perfect to be in the lead for the path of best stealth.  MacKensie can get up the wall easily to make contact with whoever in Valhiem is waiting to greet them.

If our lovely GM's dice rolls try to screw us over, then we could rely on Clive/Daisy or Adam/Bear for an emergency distraction.