Don't sweat the small stuff
I've seen or done everything from supporting boards with a bit thicker wires to nice layouts to sandwich-insulated boards [stuffed into a plastic or otherwise insulated box.
Thin wire breaks faster when wiggled around or pulled on [debugging etc.], at the solder joint/where the insulation starts. Sometimes the insulation can be easily pushed over the warm solder [when it's still warm] at the board side.
A good way to work with wire is to make a test jig with 2 jacks, 3 colored testclips [red from input tip, black ground to sleeves, blue to output], optional BP switch, easily get to the bottom of the board before installing heavy, tangly offboard parts.