Can someone weigh in on this thread?

It's a legal question but it brings up the "when do you know there's a problem" issue?

Thanks - if I can every pay back on the car/truck board (HA!) I'll be happy to do so.

https://www.askmehelpdesk.com/other-law/boyfriends-car-broke-while-driving-515677.html

I think your boyfriend is clearly responsibly for the repairs. Shifting problems of that nature usually result from poor preventive maintenance and take time to develop. They usually don't suddenly happen. Check the maintenance log (evidence) for when the manual transmission fluid (MTF) and hydraulic clutch (brake) fluid were last changed. Were the proper fluids used? If they haven't been changed in a while, there may be premature wear to the synchros. Other possibilities are a worn clutch or failing clutch slave unit. Regardless of what precisely went wrong, your boyfriend would have a hard time convincing me you were solely responsible for what happened.