IIRC the proper way to check oil level is a few minutes after engine shutoff while it's warm but has also had a chance to settle into place as opposed to splashing all over the dipstick.
It's becoming increasingly difficult to facilitate that scenario, for me.
If the best time for me to check it is upon morning startup, what is the difference in level between checking cold and checking warm.
Example: bone cold is at the Min marker level = after warm up would be at the Max marker level, etc?

 

I wish I had a good answer for your particular bike. I don't understand why the MoCo has to make this so difficult. My 1997 Dyna is the only bike I ever had that on the dipstick clearly shows FULL COLD and FULL HOT, makes this a lot easier.

That said, you usually want right in between the the add a quart line and full, when COLD.

 

what i've been doing is adding a 1/2 quart whenever the level gets close to the Min when cold

 

Cold should be between the low and half way mark. When checking it should be hot not warm and the cold check is really just a safe to ride mark to get it warmed up. Relax it is not rocket science. Over fill it cold and you will experience oil loss through the AC.

 

Any reason why it is difficult for you to check your oil when you get home from riding?

 

Check the level hot and cold and make your own marks.

 

Why is it becoming increasingly difficult to facilitate that scenario?

 

Holy $hit some people try to make rocket science out of any process.

It`s checking the oil on a motorcycle, for cryin out loud...