p4wnc6 comments on More shameless ploys for job advice - Less Wrong
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Isn't one of the main points of insurance specifically to have financial security for things you can't predict? Hedging against health risk? I don't think I will be abnormally prone to dental problems in the next year, but we're also talking about lack of dental insurance for the next 3-4 years, over which it is more likely that I will need things that would massively cheaper with insurance than without. I also don't have much of a lifeline with extended family; they couldn't really afford to help much.
I went without a dental appointment for 13 years before this one. I've heard similar numbers from many friends. You may be overestimating the likelihood of a problem, especially if you are young. Are your wisdom teeth out already?