Well, it's fully possible to be self-insuring in these areas. Prescription assistance is probably the one significant benefit as physio, mental health and the like can be of limited reimbursement (judging from what I've seen).

The key issue is that the core of one's health insurance is not dependent on the employer or even being full-time employed. This provides tremendous flexibility. And I suspect not having things like pregnancy being seen as preexisting conditions is a big win for parents-to-be.

Age or low-income (I think) provide provincial or federal assistance independent of employment also. Medical expenses are also far easier to deduct on taxes in Canada vs. the US.

Doesn't it seem likely that tax treatment has more to do with this than benefits? People are reading this like YC isn't investing in companies HQ'd in Canada, but there's no evidence of that! I look at a set {US, Singapore, Cayman} and what I think is "this is about taxes". Maybe especially tricky for YC since such a huge fraction of their portcos are pre-revenue.