is calibrating the speed and gear position necessary when running a gear specific PCV Map?

Yes, it's necessary. There's no Way to get around it.

Is there a way to manually enter the values, I don't see the point of downloading a gear specific map if you still have to throw it on a dyno to calibrate speed and gear position. Is there a problem with running a gear specific map without calibrating?

Doesn't have to be done on a dyno. You just need to get the rear wheel of the ground (making sure the bike is secure) and run it in gear. It takes about a minute to do.

ah that makes sense. I'll give that a try, thanks!