It depends on golf course policy. I used to know my regular caddie quite well in Chiang Mai. In Chiang Rai, it seems all courses have a policy of rotating caddies, and one has to pay quite a lot extra for a regular caddie.
I suppose when there are 100 caddies at a golf course, all wanting work, the policy is equitable. However, it does prevent a golfer and caddie getting to know each other well.
Another downside is not knowing whether one is going to get a good, average or incompetent caddie.
All the caddies at the course where I am a member seem to know me; be damned if I could remember them all if I was 50 years younger.