Mark,
I took a look at the most recent file you posted. My observations/issues:
- only the top is ID 2, all of bottom and all of the side, except for 1 polygon, is ID 1, one polygon on the side is ID 3! I would make the top and bottom the same ID.
- both UVW map modifiers are planar. The cylindrical side should have a cylindrical mapping.
- If you change the display to Wireframe you can see that the gizmos are not correctly sized or aligned. I deleted both UVW Map modifiers and recreated them. The gizmos defaulted to the perfect size.
- The material editor had the Use Real-World Scale boxed checked. This should NEVER be checked! and the UV values for the material and the gizmo should start at 1, you had a very small value for the material.
- I am not sure how you want the image for the side of the cylinder to appear. If the image needs to be rotated by 90° you should not rotate the gizmo since you are using cylindrical mapping and you want to keep the cylinder gizmo appropriately aligned. If you don't want to use the w value for the rotation than I would just create a new image file by rotating the image 90°. I have done that. Put it into the correct folder when you go to use it.
Good luck.

lee.minardi