My thoughts:
Bugs Bunny vs. Phoenix Wright
Selling cookies: I see Bugs Bunny with an advantage here, he makes a damn good mascot, but maybe pheonix wright could lawyer people into buying cookies.
Pranking: Bugs Bunny Advantage
Crime Scene Investigation: I'd give it to Phoenix Wright, who has enough experience with the justice system to know at least a little about forensics.
Taskmaster vs. Dreadnought
Locating Ancient Artifacts: I'm not quite sure he as of yet, need to think about it
Causing Chaos: Advantage Dreadnought i think, he could easily walk into a populated area and just start destroying stuff, Taskmaster could cause some destruction too, but there's a lot of shock factor that comes from a 2 ton death machine tearing down buildings and electrocuting power stations into uselessness. Then again, Taskmaster could potentially create chaos in a more subtle way, like training a rebel army or performing a string of shocking crimes.
Raising Children: I never thought i'd say this, but i think taskmaster might be better at raising children. It's been proven before that having a cold metal contraption as a parent causes some crippling psychological problems (at least in monkeys anyway), Taskmaster might be a terrible parent, but there's nothing like flesh and blood. Also, you can bet that that kid would have some bitchin martial arts skills.