[Dailydrool] Help! Advice needed on flying bassets

[Val Brewer]

Aloha,
  Like a number of other droolers (hi Esther), we've been out of work for a couple of months--layoffs. Arrgh.  My husband just got a new job offer, however, this week. Congratulations, DH.  But...the new job is on another island than the one where we now live.  So we must move, alas.  Bill must move right away.  I will follow with bassets and cat when we can figure out how to manage housing and other such details.  (Probably this will be a few more months--Nancy, we are still delighted to have a basset rondezvous with you in  Jan.).
  My question is--how should we manage the basset flight?  Both my boys, Harley and Bo, are claustrophobic and crate-phobic (they are multiply pre-owned rescue hounds with too many past hours confined to crates, such that they are basket cases if confined in close quarters--e.g., at the vet's they have barked and howled continuously and needed special handling for even short stays for teeth cleaning, etc.).  The flight from Oahu to the Big Island (Hawaii) which we will need to take will be relatively short--a couple of hours counting airports--but neither will do well and both will be panic cases.
  I would be interested in advice on tranquilizing the boys (how, what,how much, how soon--of course, I will ask my vet as well); also on whether it would be better to crate them together than separately; and whether I should start some sort of advance behavioral training now, or just wait and zonk them out in a couple of months when the necessity arises.  I am a mild basket case myself (I hate moving).
  Also, any advice on acclimating them to new places? Harley, in particular, freaks out with any new situations (we are his seventh owner and the reason the owner before us handed him off was that he "doesn't do transitions").
  Any help would be greatly appreciated.  Thanks so much, Val