Hiya,
JT, I cannot deny that to secure a post in a top-tier area/ or club, it helps immeasurably to "know somebody." However, my experience is that the best type of reference for a "cold-call" of the sort you were referencing in your LA time, is to have letter(s) of reference from some authoritative source nearer your home...a club president, a former caddiemaster, a home pro, an industry figure of note.
And you know how you get those? By being a competent caddie for some measurable stint in the "minors" first. That is the 800 lb context gorilla in the room in making this attainable desire into a reality.
Even with a superb background in golf, an able body, and a long-ago history as a caddie working your way through college (or caddying for a few good amateurs/pro buddies in tournaments) you are not going to hop off the couch and just start pitching in the major leagues at a place with brisk business. How the hell does one know if you are going to be worth the trouble?
One ad-hoc function I perform besides looping at WF (where I only make 25-35 of my annual 80-100 loops) is occasionally helping the caddiemaster, nearly a career-long personal friend of mine, screen the 10-20 inquiries he gets from afar...ever year he gets "resumes" from GBI and Europe, other great courses in the States, etc. We both look at these things, and see so many that are "thin" - just perfunctory...a guy you can almost hear the applicant saying, "Hey that would be cool to caddie at WF...I hear they pay good..." when they don't realize he really calls these places up and talks for a half hour on the phone or several emails.... Knows the great roster of courses and noted caddie programs, where his members play elsewhere, and asks about their experiences at club X where the app is coming from, whether that member thought the caddie program there is any good at all, etc.
I admit that potentiates really have to "hunt" him down, but that's the way he wants it; and in all but in one case did the doggedness with which he and WF were pursued by Candidate X make the final call on a new guy, who had otherwise competent credentials.
I'm pleased that you see my attitude towards the job as rare, because I think it is; yet along the way, I find that the most able of caddies I've served with had some central holding just like it...we like the game and we like the people who like the game enough to share it with us for sustenance.
But I fairly conscious of why that is, and how exactly I arrived at this disposition. And yes, there are times when I don't feel so lucky, and its usually on the way to the club, or leaving it...and I'm thinking about money woes and loop money that's already spent...rarely on the course itself. I have never rejected the investment of a person wanting to have a good day, but I occasionally have either failed or turned into a silent bag-toter to a man that could or would not be reached. As I advance in years, I'm not so eager for the odd novice who picks up at 9 on every hole as I may have been...and I caddie less and less for 50-80 year old women, so I do not become discouraged (that's one allowance my veteran status affords me).
Oh yes, and the second loop on the three (3) holiday Mondays (Mem. Day, 4th of July, Labor Day) is chasing carts for 6-somes, 3 husband-wife pairs, sometimes playing with an opposite spouse, Pinehurst, 1 gross and 3 net prizes, by 6-some, and by pairs, so every hole must have a result...in recent years my tolerance has gone way down for this by the 7th hole of the day. Last year it started to rain on our 5th hole of the shotgun...I had them in the clubhouse with two atomic-stiff drinks in their hand before they could even say the word, "Umbrella..."
cheers
vk