Does a PlusPower work with Hitmonlee's Stretch Kick attack?
It does not. Pluspower only adds to the total if the attack does damage to the [Active] Pokémon only.
Source: WotC Chat (2000-05-11)
If the Defending Pokémon has a status change (like Poison) but an attack requires you to flip to see if the same condition is afflicted, do you still have to flip? (Eg - Weedle's Poison Sting reads "Flip a coin. If heads, the Defending Pokémon is Poisoned.")
Yes, you have to though I can understand why you would consider it redundant.
Source: WotC Chat (2000-05-11)
If my Pokémon fell asleep and it wakes up next turn, will it be able to attack on that turn or the next?
You flip at the end of each player's turn. If it wakes up after the other players turn, BEFORE yours then it would act normal on your turn.
Source: WotC Chat (2000-05-11)
If I have Zubat (no retreat cost) as my Active and retreat him, can I bring him back as Active or do I have to bring up another Benched Pokémon?
When you retreat a Pokémon, you are swapping it (a switch) with another on the bench. So in this case, Zubat goes to the bench, and you bring up a different Pokémon from your bench.
Source: WotC Chat (2000-02-17), WotC Chat (2000-05-11)
If I have 2 of the same Pokémon in play that have a Pokémon Power [or Ability], can I use that power twice? What powers wouldn't be useable twice, or more for that matter?
Sure, depends on the particular power though. If you had two Muks for example, then only one power is necessary.
Source: WotC Chat (2000-05-11)
Can I have an English Dark Blastoise on the side while having a Water Energy with Dark Blastoise written on it in my deck and play it in a tournament?
No, you'll have to use the Dark Blastoise.
Source: WotC Chat (2000-05-04)
When Smokescreen stops an attack, does it stop all effects of the attack, even those that might be done to the attacking Pokémon?
Yes, it stops all effects.
Source: WotC Chat (2000-05-04)
What about cards that do not state when the effect ends? Like Fossil Magmar's Smokescreen? I think for only one turn (the opponent's next turn), but some Apprentice people say it lasts until Magmar is Benched!
The effect says tries to attack during your opponent's next turn, so it only works on the next turn after you use the attack.
Source: WotC Chat (2000-05-04)