In explaining the final chapter, is Winson's experience better for being sent to room 101 or more bleak because of it?
I think that the ending to the novel is a complex one. Winston has become like everyone else. He has a job that enables him to make more money and he has found a sort of comfort zone in the Chestnut Tree Cafe. He has his chess game, his gin, and has managed to find a domain in which he can live his life. Certainly, Winston's constant railings against Big Brother is noticeably absent and he is no longer seeking to destabilize the control of the external authority. There is something to be said about his state of being in which "everything was all right, the struggle was finished." This might be indicative of how Winston's experience is better off from having to endure his time in Room 101.
Yet, the reality that underscores the final chapter seems to be more troublesome. Consider what Julia had said to Winston earlier on in the narrative:
‘They can’t get inside you,’ she had said. But they could get inside you. ‘What happens to you here is FOR EVER,’ O’Brien had said. That was a true word. There were things, your own acts, from which you could never recover. Something was killed in your breast: burnt out, cauterized out.
This becomes the haunting reality of Winston's life in the final chapter. They, the Party, did get inside him. The Party got inside of Julia. In her "bald" admission of "I betrayed you," and in his saying the same thing, there is pain in the condition that Winston lives. Winston's life is one in which he is "burnt out, cauterized out." Winston is the checkmated black side of the chess board. White always wins. Winston's life is punctuated by "false memories" such as the one with he and his mother playing board games. In the end, Winston is a shell of what he used to be and his admission in the end, the tears he sheds, is the official death of resistance. With a condition of a silenced voice, I think that there is a pain within Winston's being, something that has made his life fundamentally worse since entering Room 101. It is this bleakness that ends up being the final goal of Big Brother in the government's control over its citizens. This reality is what makes the ending so devoid of hope and redemption.