I've ask this question before and I hear it's not good to changethe engine oil to synthetic before the break in period of 1000 miles. But I can't see where it would hurt the tranny.
I switched to Amsoil synthetic gear lube 75W 90 in the tranny,man what a difference.Both Amsoil and Harley recommend gear lube for the tranny although you can run 20W 50 engine oil the gear lube works better for me anyways. Use 20W 50 Amsoil synthetic in the engine, engine runs quieter.Thats my 2 cents worth
I also switched my tranny from Amsoil 20w-50 to Mobile 1 75w-90 syn gear lube. Shifts are quieter & smoother. I've also switched both oils from Amsoil to Mobile 1 just for convienience. I got tired of trying to find Amsoil when on the road if I needed to top up the oil level.