Ebbie
caroling for money is fairly old in GB. If you read Thomas Hardy ( late 19c. ) it was the tradition for the village band and singers to go and entertain the people at the big house and be fed afterwards.
In the c.20 in Gb caroling was a bit like trick and treating. The local children would come round and sing a few carols outside the door and if you gave them mince pies or a few coins they went away.
Some groups would do the same for a charity.
Today some people put on xmas shows that include carols and get paid for it. We did one of these at the end of November in an acual church - a mixture of well known folk songs and carols that everybody could join in with, and mulled wine and mince pies during the interval. The church charged £7.50 on the door ( about 10$ ) to raise money for the 12 centuary church as well as enjoy themselves.
I expect the knowledgable people on mudcat can come up with earlier references to people singing carols for money.
FloraG