Once Undercover Butler's ability triggers, it doesn't matter what happens to players' life totals before the ability resolves
Jandor's Ring cost way too much to play, and Jalum Tome itself is usable only once per turn, but Compulsion can keep you cycling through your deck as long as you have and a card to pitch away each time
For the second clause, you need to sacrifice it

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No way will you play this card in a friendly match and risk damaging it
Captain Hook, Forceful Duelist has a resource cost of only 1, attack power of 1 and a defense rating of 2