Rule 1) This is a game entirely based on skill.
Pokemon
Tyler
Disney
Wild
100

Free Win

+100

100

The Main Character of the Pokemon Series, Ash, has this furry companion as his main Pokemon

Who is Pikachu

100

The Most Intelligent and Interesting Man in the World

Who is Tyler?

100

This Disney Princess grew up "Under the Sea" in Disney's hit movie "The Little Mermaid"

Who is Ariel
100

The Names of Tyler and Sarah's Feline Friends that they recently adopted. Nicknames are acceptable answers.

Ativan and Pnuemo (originally named Caviar and Champagne)

200

Free Loss

-200

200
Name Pokemon that has not been said yet by us today

+200 / -200

200

Tyler's current EMT license level

Advanced Emergency Medical Technician (A-EMT)

200

This Disney Princess Movie features its Disney Princess in the Title, and is often complained about its historical accuracy and depiction of Jamestown Settlers.

What is Pocahontas?

200

Sarah's Favorite Holiday

Halloween

300

Higher Number

+300

300

Name a Fire Type Pokemon

+300 / +300

300

Tyler's Favorite Holiday

Halloween

300

This Disney Prince rescued a long haired blonde from a tall tower and was a well-renowned criminal in the movie "Tangled."

Flynn Rider
300

The number of direct family members Sarah has, including herself

What is 7?

400
What number am I thinking of?

Because you said the number, I am now thinking of it. +400

400

Name A Flying, Ghost, Ground, or Poison Type Pokemon

 +400 / -400

400

Name non-medical certification that Tyler has

+400 / -400

400

This Disney Prince kissed and woke up Sleeping Beauty

Prince Phillip

400

How long have Sarah and Tyler been dating?

9 months tomorrow

500

Heads or Tails

Tails

500

It is a long-running joke that no matter how long the Pokemon series runs, the main character Ash is always this many years old.

What is 10 years old?

500

Tyler's Favorite Color

Blue

500
This bunny rabbit was Mickey's predecessor

Oswald

500

How many federally recognized holidays are there in the Washington D.C. area?

12: New Year, Martin Luther, Washington's Birthday, Memorial Day, Juneteenth, Independence, Labor Day, Columbus, Veterans, Thanksgiving, Christmas. 

D.C. Bonus: Inaguration Day