I had to attend a destination wedding las summer, and I was highly annoyed by it. It was in Telluride, which is ludicrously difficult to get to, and expensive. We have flexible schedules, so we found cheap plane tickets to Denver mid week, and made a camping trip out of it on our way there and back. But for the wedding itself we had to stay in an expensive lodge. We did share with friends, and it had a kitchen, so it wasn't as bad as it could have been.
I felt bad for our friends who work normal jobs, as they had to take Friday off, fly out super early friday morning, rent a car, and make the drive, which took 8-9 hours due to the friday afternoon traffic and summer road work. They got the lodge at 9pm Friday, attended the wedding on Sat, and left at 8am Sunday morning to drive back to Denver to make their flights home. And they probably spent as much for the weekend as we did for the whole week of travel.
I had a destination wedding 18 months ago that was just for immediate family. We realized that for what we would spend on a venue for 6 hours we could pay for an entire week's vacation, so we did that. We put everyone up in a villa with a stocked kitchen and a chef, a pool, and a gorgeous garden/patio, so it was just plane tickets that people needed to purchase. We paid for our own tickets with miles, and I ended up buying my sister one with miles too because she's broke. My parents paid for their own, and my husbands parents covered his various siblings' tickets along with their own. It was great.