How does WInston feel about the world he lives in and how it is run?

This depends on where in the book you are referring to. For part one, Winston violently hates the party and his pathetic existence but he has learned to turn off his emotional existence. He drinks Victory Gin which helps him dull his emotions.

He crossed the room into the tiny kitchen. By leaving the Ministry at this time of day he had sacrificed his lunch in the canteen, and he was aware that there was no food in the kitchen except a hunk of dark-coloured bread which had got to be saved for tomorrow's breakfast. He took down from the shelf a bottle of colourless liquid with a plain white label marked VICTORY GIN. It gave off a sickly, oily smell, as of Chinese ricespirit. Winston poured out nearly a teacupful, nerved himself for a shock, and gulped it down like a dose of medicine. ch 1

Much later in the book, after his "re-education", Winston is a very different person than he once was.