Tape guide, if the lock paint is original leave alone. Tape guide is fixed, not related to the head bridge and not the cause of your problem. In regard to head bridge, there's only one thing to check: if it moves all the way into position or just partially when the plastic slider pulls it up. However given what you say about takeup torque being very high, incline towards that being a problem rather than the pinch roller. Of course fact it sits at an angle should be solved later on, but not the main concern right now. Likely issue is clutch is frozen or touching something and can't slip properly.
Yeah on a second inspection the whole pinch roller is making contact when it play (and powered). I made the mistake of seeing that when the walkman wasn't powered and thus didn't pull the head unit forward. Checking the head bridge and the slider it does move it all the way up. What should I be looking for with the clutch assembly. I'm not quite sure based on the service manual which parts I should be looking for. I assume I'll need to take the takeup gear off to see below it. Adding some images finally of the board and motor assembly:
