I've come to the conclusion that working with snap guide off is usually the best way. Shift works normally without snap guide on, and rotation is done easily enough. The snap guide could need a rework, not only in regards to rotation. The large circle that extends from origo makes working in snap guide more and more hopeless the further away from origo you work, as the snap guide believes you want to snap to the circle when moving objects in a straight x or y line (even with shift). Snapping to a imaginary midpoint between two snap circles is also frustrating and unreliable.
This is of course a matter of preference I'm sure, but even factoring that doesn't account for the lacking intuitiveness in certain situations with snap guide on, or the lack of options and settings within the mode.
So to conclude, my solution to the specific problem in this post is to turn snap guides off and work without it until you need it specifically. Snap points are usually enough and it consistently works very well and "understands" the user's intentions. I no longer miss a quick 90° rotate command, as shift is functional and quick when snap guides are off.
