Best way to Rotate Textures Repeatedly without Texture Transform Tool?

I’m constantly creating boxes with wood grain textures. Invariably once I paint the face of an object with the grain, every side piece is facing the wrong direction of the grain. Obviously I can use the texture tool side by side and adjust every side.

Is there any trick to either telling SU that I want all the newly painted sides to go a certain direction or build the initial object differently such that I can make the grain point differently by default?

Last, is there an extension that makes manipulating texture orientation a bit quicker?

After rotating, you can try right-clicking and selecting “Create unique texture”. That should give you a new material with a different orientation. Tiling might get confused.

Would SU wind up using the texture twice and by way of that adding 2x the file size of the texture? I’m always leery of adding too much weight to my model with textures but curious if this would not apply.

Yes and no. SketchUp creates a new texture image based on the face you have selected. So yes, it increases file size but how much, depends on the size of the face.