It is random, and it is set in stone once you catch the Wurmple. It is related to the Pokémon's personality value (which is hidden and completely inaccessible through normal means) and has a confusing equation, and has the same effect as the first sentence. Contrary to popular belief, Wurmple's evolution does notdepend on time of day, gender, or any other stats.
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Silcoon evolves at level 10, as does Cascoon.
NO.
Jigglypuff will evolve into Wigglytuff with a Moon Stone.
It will evolve at level 48
Lombre can evolve into Ludicolo with a Water Stone (Lombre can also be traded to evolve).