My bike is Trek Crossrip Elite 2014 and has VP-A61ACK headset on it and recently changed the top cap to "First" cap.
The problem is because of my new second-hand stem which is the Ritchey WCS C260 has a rounded hex bolt and very hard to take it out from the steerer tube and after I tried putting it back I guess I've done something to it. There is a gap between the fork tube and the (cup?) which is after putting the cartridge bearing and the compression ring and no matter how hard I push there's always a gap.It's more likely the cause of the compression ring, it didnt sit fully into the cartridge bearing. Second, after messing up with my stem I cant seem to tighten my headset enough, I tried loosen the stem bolt, tighten the top cap bolt and tighten back the stem. There's always a play where the frame connects the headset (front brake, front and back method).

Please help me out, thanks!