re: What Premier League team should I root for? (NSFWish I guess)

Here's my biased answers for Everton:

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Semi-underdog

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Yes. It's been since the mid-1980's since Everton has won anything significant, other than the 1995 FA Cup.

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At least 2 or 3 young soon to be superstars. I want to be the guy that gets to say "yea I watched _______ his first year at _______" with pride

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Roberto Matinez's first season as Everton manager was last year and he used young players regularly.

Stones (20) Backup CB. Was solid last year when called upon
Barkley (20)Starting attacking mid. One of England's brightest young stars
Lukaku(21) Starting striker. Just bought him from Chelsea but he played for Everton on loan last year.
McCarthy(23) Starting central midfielder. Hustles all game and destroys players when needed

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A cool factor, including history and other stuff that is "cool" about them

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1. Only EPL time that has Umbro as its kit (jersey) maker
2. Anfield was Everton's home stadium until John Houlding, owner of the Anfield stadium, tried to make a large profit off of the team. The Everton committee moved out and Houlding created his own team, Liverpool FC (He first tried Everton Athletic but was denied). Not so cool but just wanted you to know not to pick Liverpool.

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Minimal threat of accusations of bandwagon jumping

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There's a slight chance you could be accused of this, but just say you love Timmay Howard