Your very first rule is: "Spans MUST contain text between the two styling directives" which leads to '**' being unstyled. The question is whether the middle asterisk in '***' counts as text (and by extension, multiple middle asterisks.) Another rule is: "Spans are always parsed from the beginning of the byte stream to the end and are lazily matched" which means the first possible match is the correct one, leading to your example '*strong*plain*' - this is essentially the same as '***' but with intervening text, and the first rule requires that intervening text, so these are invalid directives (open followed immediately by close, without intervening text, followed by a dangling open.)
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