I like a big ending. One last song to bring everyone together. It's a great way to cap off a great day. This involves having a stop time at an hour when the guests will still be present.
Be realistic about how late your guests will stay. A destination wedding where everyone is sleeping on-site can usually handle a later stop time than an in-town wedding where it's easier for guests to peal away. If your crew can handle a long haul party, and some can, consider a window for stopping and play it by ear.
It bums me out to have a handful of drunk stragglers for the last song instead of a big group of friends and family. Consider going out BIG and taking it to an after party location. And don't forget that you're gonna need time to clean up!
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