How do you shorten a document that feels bloated

Delete every sentence that restates the previous one, then every adjective that would survive being wrong. What remains is usually 60% of the length and all of the meaning. If a paragraph resists, it is doing two jobs and wants splitting rather than trimming.

When you stop noticing it. If it has not surfaced a problem in six months, it is either solved or it was never the bottleneck you thought.