Hi, hope you are well.
Weight loss is not just about calories in v calories out - it is a complete misdirection. Take a look at my post here: viewtopic.php?f=656&t=7482
Instead I would look in the first instance to:
Eat only when hungry. Stop eating when no longer hungry. Drink only when thirsty. Our bodies have exquisit feedback systems to ensure we consume what we need and when. Work with your body rather than against it.
Eat natural whole foods properly prepared. Look to foods that are highly nutritious compared to the energy they contain. Think 'man-made=bad' and instead 'nature=good'.
I guess you're having fun with your insulin, so you need to bring that under control. You'll be mostly told to eat low GI and low GL, yet, this is just part of the story. There is something called the 'insulin index' which looks at the insulin response to food. It isn't just carbohydrates that release insulin...so I would suggest looking to eat low on the insulin index.
Taking it further, there is a growing body of science research giving evidence pointing to diabetics having great results from going low carbohydrate, and even into something called the ketogenic diet. If I had diabetes I would look towards reducing my carbohydrates down to around 50g a day and see what happens from there.
I may study this area in depth, yet I am not a doctor, and if you are diabetic you will be under your doctor's management. I would make him aware of the contents of my post, and ask for his opinion. If he hasn't heard of these approaches before my advice is to advise him to do a quick bit of research - pubmed.com has a growing list of studies supporting their efficacy. Any approach you do however needs to be in accordance with your doctor's input.
Hope this helps!