I don't want to belabor the obvious, but visa answers will of course depend on your route. For example, Russia no, China no, and much more. Tajikistan no, Kazakhstan yes. Iran no, and again much more. Etc.
I know less about insurance. The general rule worldwide is that if you need it there's someone waiting to sell it to you, but there are exceptions. Sometimes this, too, depends on your route, i.e., one border crossing will have insurance for sale while another will not.
More specifics = better answers.
Hope that's helpful.
Mark
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