I have had an amazing experience caddying for the last 4 years (full and part time) out of Quaker Ridge in NY. I started looping at Quaker the summer before my senior year in college while splitting time on the maintenance staff, trying to supplement my golf course architecture education as I had just finished an internship for Mungeam Cornish Golf Design. I couldn't have possibly asked for a better experience.
I have teed it up there nearly 100 times, played numerous rounds with members, had dinner in the clubhouse after invitations to their weekly skins game, and been invited to play a few of the best courses in the world that would have some members of this discussion board doing unspeakable acts for the same chance! Even over the last 2 years where I looped on the weekends while working golf course construction full time, I loved spending my weekends looping, not just for the money, but because I truly enjoy it and get treated so well by 99.9% of the members... I am by no means the only one from Quaker who has stories like this, although my passion for their golf course, and golf architecture in general certainly never hurt, I could go on and on about some of the amazing things that members of that place have done for some of their loopers.
Even now that I have just started my dream job in the golf industry, don't be surprised if I go back to Scarsdale to make a loop from time to time. I wouldn't have achieved what I have if it wasn't for caddying and some of the generous people who I have helped around the course.
That said.. sure there are some stupid rules that we have, non-that I like less than the implementation of the 60% polyester torture chamber that you know as the "white jumpsuit", but I could tell you stories from clubs where caddies have it way worse, so I won't complain to much!