So how can we express the sentiment “No matter how many times I warn Tom, he doesn’t listen, and (because of that) he got in trouble” ?
Sounds reasonable to me to start with sameトムさんはいくら注意しても、言うことを聞かないので, but how to finish it and make it clear that it’s トム that is now 困っている ?
But yeah, implicit subject switch are the worst, I still remember this post in the short grammar topic featuring a super fast implicit subject switch just after a て-form and it was the same kind of confusion.