1. Rearrange the letters of TRIPPERS to make a word for someone who takes their clothes off.
Stripper
2. Rearrange CRIED to make a drink.
The only think I can think of is cidar, but there is no A.
3. Rearrange OUTSIDE to make a word that means "boring".
Tedious
4. Rearrange EVILS to make four words that mean: a famous singer, jeans, exists, and coverings.
Elvis, Levis, Lives, Veils
5. Rearrange BEARCAT to make an entertainment.
Cabaret
6. Rearrange GENERATE to make a young person.
Teenager
7. Rearrange MEDALS to make a young woman.
Damsel
8. Rearrange REGION to make a word that means "to disregard".
Ignore
9. Rearrange LISTEN to make a word that means "without sound".
Silent (That's really ironic)
10. Rearrange PRECIPITATE to make a word that means "travelling from place to place".
Peripatetic (Phew! Thank god for looking at random dictionary entries)
ANSWERS:
10!