Which alkyl halide forms the most stable carbocation in E1?

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Which one of these alkyl halides forms the most stable carbocation in a E1 reaction?

Not II because it has an even number of delocalized electron pairs. Isn't I, IV and V the same?
 
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Which one is the most stable; vinylic carbocation, allylic carbocation, secondary alkyl carbocation, or aromatic carbocation? I, IV and V are not the same.
 
I is vinyilc, IV allylic, III aromatic, V secondary and II...?