I was in a really similar situation to yours and got some great advice that really helped me, and I'll share it here:
Do some industry standards research for your salary position and then put it into a document:
Your current salary
The industry standard
Your original job description
Your current role, highlighting new responsibilities
Arrange a discussion with your manager, and share this document with them during the discussion (don't send before, it gets too awkward). Mine was via zoom. I had broached the subject before and was told something like "at the end of the fiscal year" so this time I lead with: "I know you said it might be June, but I don't think I can wait that long. I believe I'm valuable and grossly underpaid, and wanted to share this with you..."
The document is important because it actually helps your manager make the case for you. My manager was pretty new to the company and it was helpful for her, and it worked! I got a HUGE salary bump.
Every situation is different, I wouldn't really bring up the insurance thing because that's a personal decision and doesn't affect how much you should or should not be paid, especially after eight years.
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