[Stiglr]

If you can isolate a properly shaped surface at the beginning and end of the handle,it would likely be easier to use box modeling techniques and just extrude the handle out, rotate the surface to point downward, extrude down and mate the end to a second surface where it reconnects with the rest of the jug. That should only involve snapping together and welding four pairs of vertices.

Booleans are messy, and often result in a bunch of superfluous vertices that you have to clean up with snap together commands and such. Box modeling and extrusion is much easier way to go.

As for the label... it looks like you've already got a bunch of surfaces properly textured? If you have to recreate it, one way to do it might be to create and slice surfaces to "carve" the shape of the label into the jug itself. By this, I mean: select two vertices that share a surface line. Vertex/Insert Vertex. Combine this with selecting vertice pairs and using Vertex/Slice Surface to create lines between them. Do this however necessary to create a border on the jug of the exact shape of your label. Then, you have a visual guide to refer to when painting a graphic based on the UV mapping. This would also save you from having to make a separate label fit the exact form of the jug, which might be tricky.

PM me if any of this is unclear, and perhaps I can help you further.