06 bob.

When cold, grinds into gear unless I start it in gear.

Will still do it when warm sometimes, next time it will click. Ya never know.
Running HD oil in it. primary that is as well as tranny.

Had the tranny recall done, been worse since. Have not reset clutch to my like yet.

To me, it acts like sporty would when primary chain loose.

 

In cold or warm weather, I always let the bike warm abit, mine is carb 04 fatboy, and then I pull the clutch in a couple of times, then shift to first, still a little loud but fine to my ear.