loading from the bag but it sure seems awkward
Practice. Train/Practice. Try to avoid doing it any other way. If you don't have to load from the bench for the flat range line shoots, don't. The more you do it, the less awkward it will be. You will get used to doing it and you will develope methods that work for you.
Personally, I hate ball blocks, I find them awkward to hold over the muzzle and there is no good way to use one without using a short starter, which I don't need and don't want to need. More crap to carry and one more thing to be reliant on that could be lost.
I shoot right handed. My bag and horn hang on my right side. The only thing that changes between range work and hinting field is the height of the bag and horn. In the field the bag and horn are very high to reduce movement. On the range I drop them about 2 inches for easier access.
My powder measure is either hanging from a leather thong with a loop that fits tightly around the spout of my horn, or it's in my shot pouch.
To load the heel of my stock is on the ground behind and to the side of my left foot with the gun angled forward under my left arm so the muzzle is pointed up and downrange. (This allows me to trap the gun between my body and left arm when I need both hands) I grab my measure in my left hand, pull the horn stopper with my teeth, pour powder into measure and replace stopper. Pour powder into barrel. For round ball I then grab my ball bag from my shot pouch and pour a ball into my left hand, if using a patch, (ball or shot with wads in a smoothbore is only a little different) I place patch material (prelubed) on the muzzle, thumb press the ball into the muzzle, if needed push it a little harder with the flat base of my belt knife, pull rod from thimbles and seat ball on powder, return rod to thimbles. Prime or cap, and, shoot. Wipe pan, flint, and frizzen.
Repeat.
Keep less stuff in your shot pouch. Try to keep what is there organized if you have more than just balls and patch material.
If more than just balls and patch material,, Tools and spare flints in a pouch in the bottom of the bag, balls in a ball pouch,,,,,,, I'm sure you get the idea.