From what you say, your group insurance isn’t much to talk about. Would they possibly cover an insulin pump at a better rate than what your out of pocket is for drugs? It is treated as Durable Medical Equipment. Some companies cover a lot of that cost. Then the insulin might possibly be covered under DME as well; at least Medicare does.
Also, give a look at High Deductible Health Plan (HDHP) by the numbers. You have an idea what your out of pocket is for the insulin and injection supplies, and the blood testing supplies. Add to that your annual insurance premiums, which you say is about $2000 per month, or about $24,000 per year. Then find what you would pay out of pocket if you had the HDHP plan, plus what your monthly premium is, plus the annual deductible, to see how all that compares with the way you have it now. Also consider a possible situation of a medical situation where one of you may be hospitalized, and how that would cost you with either health plan. I had HDHP for a few years and found that with all my medical needs, it was a pretty good way to go.