I applied in-person. The process took 1 day. I interviewed at Myopia Hunt Club (South Hamilton, MA) in June 2011
Interview
5 minutes, had to walk around the course for training with the golf pro. He basically showed interesting components of the course, tips to make the job easier, where to stand, etc. At the end, he provided a yardage book, bib, polo shirt, and some other caddying necessities.