In 1984 what are Winston's advantages and disadvantages of being an outsider when he starts to rebel against the party?

Technically
speaking,is an insider, at least to the extent that many people in his society are.  He isn't
one of the proles, and works in the Ministry of Truth.  So, he is technically part of the
infrastructure of the government, which makes him an insider of sorts.  He has started to rebel,
in his mind and heart, long before the novel even starts.  Even from the opening pages, we see
that Winston is unhappy, questioning of the government and the way that life is, and searching
for someone like-minded to connect with. At his apartment, he has been writing down his persona,
and rather rebellious thoughts for quite some time in a journal of sorts, out of view of the
cameras.  So, his rebellion began long before we meet him at the beginning of the
novel.

His first overt act of rebellion, however, comes in his relationship
with .  Before this point, he has only looked and people and wondered about their status, and
whether they feel the same.  He never has the courage to act on it.  Julia, when she initiates,
gives Winston hope that someone else is out there who feels like he does.  Going to meet her is
his first act of open rebellion.  Before that, he had done little things like buy the journal,
visited the prole section of the city, etc.  But meeting Julia is huge, and potentially
life-threatening if discovered.

As a person who works inside of the Ministry
of Truth, Winston has a distinct advantage in knowing, first-hand, that his government lies and
changes history in order to maintain its power.  He knows this, and that information works to
his advantage in the fact that it is something that he has over the government, but it is to his
disadvantage because it irks him, and makes him unhappy and discontented to know that is being
controlled by a bunch of liars.  So, it works both ways for him.  Because he does work where he
does, it is a disadvantage because he is more closely watched.  The proles, for example, are
mostly left alone, but Winston, because he is privy to the government's secrets, is watched like
a hawk for any signs of rebellion or treachery. That is a huge disadvantage, and one that keeps
him from being happy.

He is an outsider to the inner circle of the Party, and
that is a disadvantage because he does not get the nice things, does not have the privileges
that those members do, and does not have the truth behind their plans or the power to gain his
freedom and happiness.  It is a disadvantage becuase he never knows that he is being watched,
and so acts in ways that leads to his torture.  Being an outsider to the inner party is an
advantage in the fact that he does not know their darker secrets and so can't be held
accountable for them.

I hope all of those thought helped; good
luck!