O-rings shouldn't need to be tightened much, they aren't like gaskets, they seal when just slightly deformed. They do need to mate against an absolutely smooth surface, and coating them lightly with silicon grease often works. I haven't taken my trim pump apart yet, so these are general comments, not experience-based...
1975 32' Flybridge Sedan, twin Perkins 6-354 diesels, 1:1.53 velvetdrives, 16 X 19 props. Merritt Island, Florida