Just thought I'd throw my two cents in.
I was diagnosed with Type I (aka Juvenile or Insulin dependent) diabetes when I was 15 and have been taking 2+ insulin shots a day ever since (22+ years = a helluva lot of syringes). I've seen blood sugars in the 400s and had hA1Cs as high as 11 over the years. I've also had surgery for retinopathy (somewhat painful but it's amazing what they can do these days, i.e. that laser surgery, digital blood sugar monitors and other such things that did not exist when I was first diagnosed). My goals/plans are probably similar and yet dissimilar to yours so take from this what you will.
First of all, it's great that you are trying to get your blood sugars and weight to a happy place.
I don't recall seeing anyone mention this, but I think it would be a good idea for you to meet with a nutritionist. They'll help you come up with sensible eating plans that work with your medications (it's very important for type Is to balance the two, not sure about how close it is for type IIs). Do not weigh yourself every day, one a week is plenty. There are all sorts of factors why you might be a little heavier or light from day to day. Don't forget that muscle is heavier than fat. The fit of your clothes is a good indicator of weight loss.
Also, while it's very important to keep your weight and blood sugars (BS) under tight control; do not obsess over them. It's very easy to get frustrated when your BS or weight do not seem to always be exactly where you want them to be (a BS of 123 is still damn good). It then becomes very tempting to say, "what's the point" and not pay attention.
My understanding is that normal is usually 70 - 120 (of course it was 80 - 120 when I was 1st diagnosed). Also, there are test strips you can buy to check for ketones. Again, my understanding is that they usually show up when your BS has been high for a while as they are the result of sugars spilling into the urine.
I'm sure you've heard this all before (I know I have) but I think it's a good thing to realize that others are going through something similar to you and face the same struggles.
Tom