Hiya,
Our board is littered with people who have engaged a similar experience or swim in those waters regularly. It could well be done, within limits.
1. The idea of course hopping over the six months is nearly DOA; while some caddiemaster-starters "might" be OK with it, many would not. The basic ability that impresses most caddiemasters here (and abroad I reckon), is "avail-ability." The toughest job a club CM has is to maintain availability for a imprecise crowd, that even when they are scheduled, fluctuates. Even so, the caddie who secures such an arrangement is at the bottom of the totem pole each morning...if sitting on pines for 4-6 hours isn't one's thing. In the long summer hours of a place like Scotland, I understand that you can show up at 7 am...not get out until noon, get back in at 4:30...think you're done...and be asked to wait until 6:00 for a late-scheduled round/request, come home in the dark of 10:30...and back up at 5:30am for the next day, where you might get out once, after waiting until 2 o' clock for it.
2. That said, I have a close friend, a successful writer, who worked two or three seasons at St. Andrews, and was sometimes sent to nearby classic courses outside of the "auld grey toon" for odd assignments...so he got to see more than just one course, He knows everything about the whole of being an import into St. Andrews. If MH or anyone else wants to make a true inquiry, send it to me, as a message, and I'll have Don get back to you.
3. No matter what the technical details, the best shot one has is at a 36 hole (or greater) area of facility. If there's multiple courses on one club or within the neighborhood, there's a good chance to make it happen. the 36 hole courses I know best...WF, Baltusrol, Westchester employ caddies like M&Ms and are ready to accept such things. (Plus WF occasionally sends caddies to other courses clustered nearby when they can be spared...QR, stanwich, etc)
4. Not that this matters to the "dream" aspect of doing it, but...in Scotland, you're doing one bag (no doubles) for about $120-$150 per bag, twice a day means about $250-$300 on days you do two (which i'm told are frequent). In an American model, you'll more often do two bags at about $90-$100 per (both figures include tip), but much rarer to do two loops. But the days you are fortunate to get two assignments, it can be a sweet number, and you're sleeping real good.
5. Which kind of brings to mind the idea stated by many posters, that you're going to be "playing" quite a bit in whatever area you choose. If you're really caddying, and link up with a course and are being exercised...you have little time or energy to play much golf. It is a statement meant for intern professionals and other young golf staff, but its truth applies to caddies too, "If you want to play golf, don't get in the golf business." Through my work and contacts, I can play almost 75% of the courses in the classic Westchester-Fairfield belt...I never do. When I have really been working at golf five or six days a week, the last thing I want to see is a golf course on the sixth or seventh day.
6. Which leads to my last statement, in that I know the thread title wasn't meant in any charged or contentious sense, but I do take a bit of umbrage at the "Dream" portion of it. (I'm not accusing anybody of being an asshole, I'm just giving my perspective) I live this reality...five months caddying, 7 months adjunct teaching, with some crossover in April, May Sept and Oct. It would be more of a dream if I had some REAL money behind me or if I had the benefits of a tenure track as a teacher. As it is, I have neither and so the idea of HAVING to go pick that fruit off the tree everyday, without fail, grows more and more weighty each season. I have not been to a holiday barbeque or day baseball game in 20 years, I have no idea what people do on a summer weekend day, my yard is a mess, I haven't been to a beach since 1998. I both resent and love the rain, as a lost day and a day of rest...one injury, one torn meniscus, or Achilles's rupture, or wicked back problem (all of which is an occupational hazard) is a constant fright; I could be out of my house within 30 months if it was real bad. I haven't played pickup basketball or slo-pitch softball since the early 90s... I don't resent the term dream, because I know how much I love it and I know from where it comes. I would honestly STILL caddie 50 rounds a year if I hit the Powerball, I love it so much..but getting to serve on multiple boards with stock options-THAT is a dream...receiving $1000 every time I put my foot in a batter's box or throw a pitch...THAT is a dream. To be a department chair at a college...THAT is a dream. For these are dreams that allow many of the other dreams to be approached Caddying for six months is hardly a dream or a sabbatical in my eyes. I wish the thread read: "Sampling Something Possible I've Always Wanted to Try."
cheers
vk