Congrats on starting insulin April! I'm sure you will start to see some results soon
Don't get discouraged about the ear bleeding, it is definitely tough at first. As you continue testing, Quincy will grow more and more capillaries in his outer ear and soon it will be much easier to get a drop! What gauge are your lancets? 28 gauge is a good beginner size because it is larger, you can progress to a smaller gauge once Quincy has more capillaries

To promote blood flow to the ears some members warm their kitties ear with a warm cloth in a baggie, or a small pill bottle filled with warm water. If you definitely still can't get a drop you can prick his paws, but I believe that is more painful and you get a lot more blood. Poor Mowgli had a tough time with testing at first too, I have put the lancet right through his ear, before AND I have hit the vein a couple of times... blood EVERYWHERE! Trust me, the ear pricks are the hardest part
If you are finding his ears are getting bruised try gently massaging them with the cotton pad / toilet paper you used on the inside of the ear after you've gathered your sample, this helps disperse the blood instead of allowing it to pool and bruise, it also helps to stop blood flow. If you think hes in a little pain, you can use neopsporin with lidocane to diminish the pain.
One other thought: are you using the lancet pen? I found that harder to work with, usually i just take the cap off of the lancet and poke Mowgli myself, I find i have more control that way.
Chin up! you're doing great!