I wonder whether a 50 state strategy is viable, on game theoretical grounds.
Superficially, it would appear that the equilibrium of a system with state by state voting and winner-takes-it-all rules is a two party system where each party has "strongholds".
If we assume that the votes a party gets in a given state are, roughly, proportional to the amount of resources (time, money, volunteers etc.) that party expends in that state and that it is irrelevant whether a state is won 51-49 or 99-1, the party who evenly distributes its resources over all states would be at a disadvantage compared to a party that spends all its resources in exactly half of the states plus one.
Of course this may be an oversimplification, but it does appear as if this is exactly the situation we find ourselves in.
There may be historic reasons why the strongholds of the parties are geographically in the places that they are, but if this was not a stable equilibrium one would expect more variation over time.
On edit: Of course I assumed in the above for the sake of simplicity that all states are equally sized, which is not true but irrelevant for the validity of the argument.
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