If you quitted early into the game like in 2014 don't go for one because it would already be like starting over again if you quitted in 2015 go for one
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I might just start over again anyway because it has been too long. Also i stopped at christmas 2015
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Well you have two low leveled 40 and one that is a 36 so I say keep going it would be bad if you just restarted
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When is the deadline for transfering characters?
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I would say before rise of iron because that is when the legacy consoles will be cut off