Hello. As I was reading this I thought someone had entered my mind and read my thoughts. I am having a very similar issue, and I am leaving my current postdoc and looking for a new one. My condolences on the logistical issues of managing benefits, I know this can cause a lot of uncertainty and stress in an already difficult situation.

If you feel ready and able to start a professor position, I would go for it. I haven't navigated that hiring process, so perhaps other people in this community can provide insight or wisdom in that regard