I'd definitely remove as much as the old caulk as you can. I'd be inclined to use a good grade of acrylic caulk because of the painted return. I'm partial to the 'white lightning' brand. It is a siliconized acrylic latex caulk which is paintable.
Yes, the exterior trim could have come off and you would rip a 1/4 strip of wood on a table saw and apply it to the exterior side of the jamb. You can add the same 1/4 strip to the interior side of the jamb, but you would want to apply it 1/4 away from the inside perimeter of the jamb... your hinges and strike plate need that 1/4 reveal. The casing would then be stepped back another 1/4 from that.
I'd disagree slightly. Adding the strip to the hinged side could be problematic because of the hinge.
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