LLC help

I’m at a rubber meets the road moment. I lost my job 17 months ago and instead of chasing another one, I started my own business which I am the only employee of (Single Employee LLC) that has been successful since. I’ve been paying for Cobra insurance since at about a $700 premium monthly and I believe this is my last month I’m eligible for. I have type 1 diabetes and between insulin, insulin pump supplies, and continuous glucose monitoring, my out of pocket costs for treatment would likely be close to 20+k/yr. I have 2 questions to answer:

-How do I go about buying a plan that covers as much of my costs as possible? The largest costs are durable medical, biologique (insulin, apparently has a separate deductible from from prescriptions), blood work, specialist appointments, and to a way lesser extent, prescription drugs. Categories are listed from largest to smallest costs. I don’t mind high premiums if they keep deductibles or copays low.

I doubt I’ll have insurance for November and December and will likely have to order supplies to get through the year after my Cobra lapses. This is frustrating because I’ve already met my deductibles in all the categories for the year. How do I address this gap intelligently? Does it make more sense to pay out of pocket to the tune of probably 7-8k?

-bonus points: any advice on using the LLC to pay for insurance? Can a potion of my premiums be a business expense? Any other suggestions for taxes?

Thanks in advance for any help. If I can figure this out, I’ll have successfully broken free from the exploitative and abusive practices of my industry and created a more stable healthcare situation than I have ever had in my career.

submitted by /u/hardwoodholocaust
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