Why would a 16th century Italian painter choose canvas over wood panel?

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Tackling the final one of your questions; i.e. why would they choose canvas over traditional wood? It seems that the main reason was one of portability.

The use of canvas as a support for oil paints allowed for easier transport of larger compositions, canvas is far lighter that oak panels, also a painting executed on canvas can be rolled up and transported more easily than wooden panels. Canvas became prominent in the Italian renaissance and it was widely used particularly in Venice. Venice was a wealthy trading port and, in the many workshops within the city, produced sails made from linen and other fabrics. In fine art linen is still considered to be the finest support for oil painting. Painting Techniques of the Renaissance

Making the paintings more portable allowed an artist to expand his potential market beyond his local area. It also made it easier to produce paintings "in the field" since the key materials were easier to get to the location.

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