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1) With regard to your specific situation, I would first check your team defensive efficiency and see where that ranks (presumably it would be low, given your description). Then, go look at your individual defensive stats (I go to the lineups screen and use the preset view). What you're looking for (well, what I look for) is what guys have individual defensive efficiency below 1.000. Those are likely the guys hurting you defensively.
2) The answer is....it depends. Odds are, if you don't want a guy, the other teams aren't likely to want him either (but some might), so trading your specific player might be tough. Generally, you'd want to trade a player at a deep position so it doesn't hurt you much. Long-term, developing prospects is best (for the team and your pocketbook). Short-term, if you're trying for that one last piece to win a title, trading prospects for a star might be better.
Main thing, don't be afraid to make mistakes. In my Rangers game (first season still), I made the mistake of trading Leonys Martin for Royals CF Lorenzo Cain. It's...not turning out so well. But, you make a mistake, you learn from it, and long term let the AI beware!
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