Results

And our Contest Winner is... Naomi Cline!!  Congratulations! 
You and your family have won an all expense paid trip to Odyssey through the tape you have requested.

Here are the runners up: 2nd: Anna Bentley, 3rd: Angus

Answers

Question 1: The Six Degrees of Adventures in Odyssey (hard)

Part 1:
Tom Riley's rival in the first mayoral race was A.
A has a son B.
B had a gang that was taken over by C.
C was in jail with D.
D once worked for ?.

Answer (highlight to read): Tom Riley...Bart Rathbone...Rodney Rathbone...Jellyfish...Richard Maxwell...Regis Blackgaard

Part 2:

Thomas Newcastle accidentally killed the great-great-grandfather of A.
A has a "conspiracy spotting" friend B.
B got lost on a mission to Tom Riley's house with C.
C was told an "Old West story" by D.
D had a childhood friendship with ?.

Answer (highlight to read): Thomas Newcastle...Dwayne Oswald...Jared DeWhite...Cody...Jack Allen...John Avery Whittaker

Part 3:

Doc Morton is the mother of A.
A once had to do an English (not geometry) project with B.
B went on an Imagination Station with C.
C was rescued from a dumpster by D.
D once had an assistant named ?.

Answer (highlight to read): Doc Morton...Isaac Morton...Jack Davis...Robyn Jacobs...Bernard Walton...Simon Birtles

Part 4:

Regis Blackgaard has a brother A.
A once ran an acting class where he made B the star.
B stole a notebook from C to win an election.
C tried to help D with his English poetry homework.
D tried to be a good Samaritan to ?.

Answer (highlight to read): Regis Blackgaard...Edwin Blackgaard...Shannon Everett...Courtney Vincent...Charles Edward Thompson... Glenn Adams

Part 5:

Oscar tried to get out of gym class with A.
A found out what "selpurcs" were with B.
B went on a "fishing date" with C.
C once hid the comic books of D.
D was coached in pitching by ?.

Answer (highlight to read): Oscar...Curt Stevens...Lucy Cunningham-Schultz...Sam Johnson...Henry Thomas...Pete Flanagan

Part 6:

Eric Myers once pulled A on a sled.
A was disappointed that B couldn't give him a curly-q ice cream cone.
B once gave poor advice to C (told him not to tell his father something).
C once baby-sat the "imagination-filled" D.
D handed over a "broken" portable video game to ?.

Answer (highlight to read): Eric Myers...Scrubb...Connie Kendall...Jimmy Barclay...Lawrence Hodges...Donna Barclay

Question 2: The Books vs. The Audio Series (medium)

Person 1:

In the books she: worked at Whit's End, was frightened when some boys tried to paint her garage.
In the audio series she: was thought to be marrying Whit, helped Jack Allen find out about the Israelites.

Answer (highlight to read): She is Emma Douglas.

Person 2:

In the books he: ran the Israelites as a boy.
In the audio series he: ran the Israelites as a young man.

Answer (highlight to read): He is Billy McPherson.

Person 3:

In the books he: gave Mark a part to carry for the Imagination Station.
In the audio series he: was mayor and runs an apple farm.

Answer (highlight to read): He is Tom Riley.

Person 4:

In the books he: was befriended by a strange boy named Colin and journeyed back to see the mid-1800s via the Imagination Station.
In the audio series he: took acting lessons from Edwin Blackgaard, journeyed back to see the mid-800s BC via the Imagination Station, and investigated a strange boy with the initials D.D.

Answer (highlight to read): He is Jack Davis.

Person 5:

In the books he: became a Christian and struggled with his grandmother dying.
In the audio series he: went on vacations with his family, thought he might want to be a preacher, and went to Hawaii.

Answer (highlight to read): He is Jimmy Barclay.

Person 6:

In the books he: was troubled by a bully but showed his friends the true meaning of being "Christ-like"
In the audio series he: went to summer camp and was found to have dyslexia.

Answer (highlight to read): He is Oscar.

Question 3: (easy, highlight blanks for answers)

Connie
Connie was once in love with Jeff Lewis. (Though I also accepted Jason Whittaker.)

Eugene
Whit, Jack, and Jason all thought at some point that Eugene and fellow co-worker Connie Kendall were more than friends.
Eugene is engaged to Katrina Shanks.

John Avery Whittaker
Whit was married to Jenny Whittaker (Morrow).
Many people thought that Whit was going to marry Emma Douglas when he had his tuxedo cleaned and bought flowers.
Whit had another proposal for marriage from Margaret Faye.

Jason Whittaker
Jason was engaged to Tasha Forbes.

Jack Allen
Jack Allen was first married to Emmy.
Jack Allen recently married Joanne Woodston.

Tom Riley
Tom Riley has been married twice.  His second wife's name is Agnes.

Bart Rathbone
Bart's wife's name is Doris Rathbone.

This contest is sponsored by Focus on the Family.  Thank you to the Ultimate AIO site.