Dave an Georgina (hi Georgina),
I'm not suggesting that there weren't occasions when money was involved with singing or music, quite often, as with Georgina's examples, linked to customs such as The Wran, wassails, etc.
You can also include the competitions entered into by singers like Joseph Taylor, Sam Larner, Tom Lenihan and others, where either a cash or a (usually small) prize was given.
Travellers in Ireland sang in the streets and sold ballad sheets right up to the mid-fifties here in Clare, (the last ballad sheet here was 'Bar With No Stout' - a parody on The Pub with No Beer).
My point is that in general, singing was not a paid occupation, as it was with itinerant musicians like Carolan, and like (some of) the Travellers - though it needs to be said that singing and ballads selling was regarded by many Travellers as 'a low' occupation, little better than begging.
Interestingly (to me anyway) we recorded a long interview with Kerry Traveller Mikeen McCarthy, who went to great lengths to describe the differences in style between street singing, singing to sell ballad sheets and what he called 'fireside singing'.
Around here, not only was money not an issue, but when the annual Traditional music school started to pay singers to appear at the concerts and recitals; a number of them commented on the strangeness of being paid for doing something they'd done all their lives for nothing.
Singing and playing on 'The Wran' (St Stephen's Day), was a collecting custom, but the money was put aside specifically for drink and food for 'the Wran ball' shortly after. One sad exception to this took place in the 'hungry times' when a group of men set out one Boxing Day, found the takings so thin that they pushed on all day and into the next few days until they reached Galway where they used the collection to buy an assisted passage to America and never returned home.
A number of older musicians we have spoken to have made the comment that not only was music unpaid, but that the introduction of cash was its 'ruination'
Jim Carroll