How the F' would this be handled and how long would it take?

"A 27-for-4 spot playoff was scheduled for Wednesday morning to determine the final match-play field for the 109th U.S. Amateur Championship"

I'm just picturing 27 guys on a tee box, following each other down the fairway, etc. like an elephant hunt. Do you think they stagger them on times and have everyone wait for all 27 (or whoever is still left) after each hole?

Yes.

I was in last years 27 man playoff for 2 spots. We played 3 4-some's and 3 5-some's. 3 people made it to the second hole, one person got in after the third hole, and I got the last spot on the 6th playoff hole. It is an absolute mess with that many people to start, but gets better after it gets cut down. They had a big board with scores behind the green and you knew going in you had to make birdie on the first hole with that many people. And everyone waited until every single person finished.

I saw a playoff where the PGA club pro's were qualifying for the PGA. They had I think 8 players in the playoff and all in one group. It was pretty crazy, especially when they got to the green and started putting/marking balls. I would think they would break the groups up into 4somes and 5 somes and play the holes 1 at a time. I can't imagine 27 players in one group. I played in a shootout once with 14 guys on the first hole and it was a nightmare. Hard to imagine doubling that.

kid from my country club won one of the 4 spots out of the 27