As a CDL holder with 8 years of over the road 13sp & 10sp experience, two years of 10T, 5T, & 2 1/2t and four years of 4x2sp straight grain trucks; I believe you should shift however you have to to make a smooth complete shift, being as easy on equipment as you can be. You may have to walk sooner if you don't.
Worn but still serviceable transmissions will all have a different feel. I have driven some that worked the best after you are rolling, slide shift out of gear, then clutch once into the next gear and one that was just the opposite.