Rant: my $250 add-on warranty vs the $900 tow truck lesson

So my 2015 sedan's transmission started slipping at like 72k miles, right past the factory coverage. Dealership offered me this 'powertrain plus' plan for $250 a month, and my brother in law said just self insure the money instead. I picked the add-on because my savings account is a joke after the AC died in July. Three weeks later the tranny fully gave out on I-5 near Bakersfield, tow was $320 alone. The warranty covered the rebuild but I had to fight them for 2 days because the previous owner had a tiny oil leak on record. Has anyone else had a warranty rep nitpick maintenance history from before you even owned the car?

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