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Not really. There's nothing to be worried about as long as you have the experience and are prepared.

But truth be told - what I'm really paranoid is theft, making sure my gear gets to and from the gig and making sure the data / files come back safe.

Another agonizing thing about destination weddings is not being able to bring everything I want - lol. I always get stressed over that.

In this case there was a hurricane that hit the Caribbean and the bride had to downsize to a more expensive resort - which meant I couldn't bring my associate - which meant it was one less suite case / body to bring gear.

Oh I bet. That's a lot of expensive equipment you've got to lug around. Are you able to get insurance for it?

Yes - but the insurance I have doesn't cover rentals (which I tend to do sometimes).