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I'm looking at a large-ish area. The Privateer Press Hooch Hauler. I've looked around but I'm not sure what the best option for both printing and applying a large decal. The other thing that will happen is that I'd be cutting the decal out once applied because it's on the wooden boards of a barrel, so there will be negative space.

You can buy decal sheets for an inkjet printer, both transparent and with white background. Both needs to be sealed.
The transparent is really best for pure black, because the colour saturation will be fairly weak, which means that if you want a bright red decal you need to use the one with the white background.

One thing to note is that the sheet with the white background is thicker, and can make it harder to apply to curved surfaces and harder to "mask", as you might be able to see the raised area of the decal - Especially if you place it on a completely flat surface.

Why not use an electronic cutting machine ?

https://www.silhouetteamerica.com/shop/machines/portrait

Spiky Norman wrote:
You can buy decal sheets for an inkjet printer, both transparent and with white background. Both needs to be sealed.
The transparent is really best for pure black, because the colour saturation will be fairly weak, which means that if you want a bright red decal you need to use the one with the white background.

One thing to note is that the sheet with the white background is thicker, and can make it harder to apply to curved surfaces and harder to "mask", as you might be able to see the raised area of the decal - Especially if you place it on a completely flat surface.

Do you think the curved surface of a barrel with the wood grains will work for or against a decal?

 malfred wrote:

Spiky Norman wrote:
You can buy decal sheets for an inkjet printer, both transparent and with white background. Both needs to be sealed.
The transparent is really best for pure black, because the colour saturation will be fairly weak, which means that if you want a bright red decal you need to use the one with the white background.

One thing to note is that the sheet with the white background is thicker, and can make it harder to apply to curved surfaces and harder to "mask", as you might be able to see the raised area of the decal - Especially if you place it on a completely flat surface.

Do you think the curved surface of a barrel with the wood grains will work for or against a decal?

Without having seen the model you want to use the decals on, I would say that a curved surface with grooves in it like wood grain will very much work against it. So much so, that I would probably look at finding another solution. Maybe masking and airbrushing or even using a normal brush...Or simply freehanding.
But that's said without knowing the exact surface you're talking about.