The term stripline caused me to ask about RF or LF´. Stripline is usually a´RF topic.
Of course all two-dimensional calculations are simplifications. Keeping this fcat in mind, your cross section calculation should be correct.
I'm not aware of a technique to fill a via completely with conductive metal, however. Via plugging typically uses non-conductive (or possibly thermal conductive) fills.
Regarding the second question, it depends on which are the end contacts in your resistance calculation.