Guild win a contest, either way I'm alone here...

WYR be suspended from POTCO for a week and have all the updates that you want come out the day after you get banned or have all of your friends banned forever and have no good updates for months after?

first one

WYR have new ships or more new islands?

Depends what types of ships mate, but probably ships...

WYR be attacked by a light sloop or war frigate in SvS?

The war frigate, cuz 99% of the time, the light sloops have maxed fury.

WYR have to delete all your friends, or leave your guild and never go back to it.

leave guild because u would have better chances at finding another

WYR have peanut butter or jelly

Peanut butter, I don't like jelly.

WYR cream cheese or butter on a bagel?

Cream cheese.

WYR stuff a whole bagel down your throat, or chug a gallon of water without taking a breath?

The latter.

WYR die and go to Davy Jones' Locker, or be off to Fiddler's Green?

depends what fiddlers green is, but it sounds better then davy jones locker.

WYR have a monkey as a pet or the jail dog?

A monkey! No question!

WYR have The Monkey maim you, or the jail dog?

Monkey!!! No question to that :D

WYR have a Ps3 Or Xbox 360

( think Of the Differences xD )

hmm... Ps3.

WYR leave pirates for a year, or have your friends all leave for 3 years?

Friends.

WYR have to only use a sword for the rest of your pirate career, or voodoo staff?

Sword, nothing beat steel. However, the inclination to swords may come from my name...

WYR have only 1 all-powerful cutlass or 7 fairly good weapons?

Be named savvy swashblckler.
WYR have level cap increase, or the kraken treasure map?