I'd say my biggest stress was 1) waiting for people to book - all the people I really wanted there, did book by our end date; 2) surprisingly my centre pieces. Since we're getting married in Cuba they don't have much variety/options so you pretty much need to bring anything if you have a specific vision; 3) picking the resort; and 4) I know I will be stressing out hoping people are having a good time and that they like the resort I chose. I mean they spent a fair amount to come to our wedding so I hope it will be good and they'll like it, but at the end of the day I try to remember that they also chose to come - no one was forced so I am guessing most are coming because they genuinely want to.
I was lucky to not have anyone get mad, or resent us for having a destination wedding. We completely understand if people can't come and there are no hard feelings. What I found weird was when I've talked to people who are more acquaintances or people in passing who I've told about and comment on our decision to have a destination wedding... um excuse me its not like you were even invited or have to make a decision about coming so really what do you care?