John - I wrote this very long description of how I started testing Sam for another member awhile back, so forgive the different name, etc. I need to head back to work though, so I'm short of time to edit it. Maybe something in here will be helpful for you, maybe not, but know that whatever it takes, we are all here to support you.
One thing to note is that at Sam's initial diagnosis, the vet told me to take him home and change his food first, then come back in two weeks to start insulin if needed. So the first couple of weeks I was supposed to be figuring out how to home test, but it wasn't critical yet.
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I think the first step is just to make a pleasant and consistent routine for both of you - without even worrying about the testing just yet. I test Sam on the kitchen counter so that he's up high. Like Jackie, he won't let me stand over him, so when he's up on the counter he feels safer. Then I went through the following progression. It took about two weeks. I did each step several times each day, and each step took as many days as I felt like it needed until he was comfortable. Before you do anything, stock up on a gazillion low-carb treats. You have to be quick to give treats for every little step, even if it's unsuccessful.
1. I would set him on the counter, give him a treat, and then walk away. No attempt at testing. This was repeated about ten times each day at regular intervals. I set an alarm on my phone to remind myself. I was also on vacation at the time, so that helped. If you can't be home that much, just do it as much as you can.
2. After a couple of days, he understood that that place on the counter was for treats. Then I started putting him on the counter, gently holding one of his ears for as long as he would let me without scaring him, give him a treat, and walk away. Sometimes I would give him a treat, and then hold his ear again for as long as he would let me, and give him another treat. I wanted him to associate having his ear held with something positive (the treats). I would also use my other hand to scratch his chin during this, which he loves. Repeat as many times each day as you can, with a few hours between each time.
3. I made a little felt heart and filled it with rice to use to warm up his ear. A lot of people just put some rice in the toe of a sock - I just wanted it to be cute. I would put it in the microwave for 30 seconds (the time depends on how much rice you're using - you want it to be nicely warm, but not too hot). I would put Sam on the counter, hold the rice heart on his ear for as long as he would let me while at the same time scratching his head, chin, kissing his head. Then when he indicated he didn't want that thing on his ear anymore, I would give him a treat and walk away. The reason I did this step was that warming the ear is a really really important step in getting a successful test. Their ears don't bleed very well in our chilly climate up here (Seattle), so this was an important step. If you live somewhere warm, you might not need to do this part. Repeat many times each day.
4. At this point, it had been almost two weeks of just creating a happy, relaxed routine for both of us...so onto the next step..... I took the lancet out of the clicker thing and just used the little plastic lancet by itself. He didn't like the clicking sound. So I did all of the things in step 3, but then added our first poke. I put a folded cotton square against the inside edge of his ear, and poked the outside edge of his ear. It made a little buffer so I didn't poke myself if it went all the way through his ear (which it usually did), and helped keep his ear in place for the poke. He shook his head and bit me, but he wanted the treat which he now strongly associated with this routine, so he sometimes he didn't run away. I gave him the treat, and we were done. Didn't get any blood, just getting him used to the poke.If I had been able to get a test at this point, I would have, but the poke most often lead to a hiss, a bite, and him bolting under the bed. One note is that the treat was left on the counter. I didn't give it to him under the bed. He had to understand that staying on the counter was part of the treat deal.
5. After a couple of days of that, i really wanted to get an actual test, so after I poked, I did hold him very gently to dissuade him from leaving, and squeezed his ear to get a little bead of blood. Our First Test! Hooray! If he had resisted my little "hug" I wouldn't have pushed it, but he was okay with it that day - and was rewarded with extra treats.
But seriously, it was almost three weeks from the time I decided I really wanted to home test until we had our first successful reading. You just can't rush a scared kitty.
One important note: You want to get lancets that are thick, not thin. I know that sounds more painful, and I resisted doing it for a long time, but I've found that one successful poke is so much better for Sam than several failed pokes with a thinner lancet. I used 26's. Once Jackie's ear learns to bleed, you can switch to the thinner ones (usually 30's). The more you test, the easier it is. Their ears really do bleed easier as time goes on. The first few weeks of tests are the hardest.
In the weeks that followed the first successful test, there were a LOT of failed tests. Either I just couldn't get his ear to bleed, or he would take off, or I didn't have the balancing act figured out between poke, squeeze, getting the test strip against the blood spot, etc. He still got a treat - even if I didn't get any blood. That consistent positive reinforcement is essential to making this work. It took awhile to get it all figured out. And I was on summer vacation (I was a teacher), so I had time to go through those routines several times each day. If you work all day, it's more realistic to maybe do two in the morning (right when you get up and right before you walk out the door), and maybe a couple more in the evening.
When I first started all of that, I posted in the forum constantly asking for advice and trying what was suggested. Every cat is different (you'll hear that a lot around here), so what works for one cat may be super helpful for another, or not helpful at all. Sometimes advice that I thought was dumb ended up being incredibly helpful (the rice sock for example).
Plus, I had to get over my own anxiety about hurting him, and about scaring him. The calmer I was, the better things went. When I was doubtful or nervous, it didn't work. Sometimes I would need to take a minute to breath deeply and calm myself first, so I could be a reassuring, confident presence for him. It really does make a difference.
Like I mentioned on your post in the forum, at this point he likes testing more than I do. He still winces when I poke his ear, but he loves the attention and the treats so much that he puts up with that quick second of discomfort.
Hopefully something in there will be helpful to you. Or at least knowing that you're not alone, and that this is a slow and sometimes difficult process for many of us. Those videos that show you how to test make it look so easy. I totally laughed when I first watched them because I knew there was NO chance it was going to work like that with my wild kitty.
Please know that we are all here for you and are more than happy to support you in any way we can.
. I received my YA bag a week ago and even though my boy isn't on it 100% yet I have noticed he is not gobbling it all up after his meal, like he did with just the DM.
. Are you having problems maintaining his weight? Most of us are trying to put weight back on our FD kitties.
. What is his feeding schedule like now? How do you know those are his daily numbers if you haven't tested in 6 days? 
Not trying to be mean, just confused with that.
