You've got an entire family going after you, and frankly the only reason you're ahead in one of those raids is because you're clubbing seals and flying around to avoid being hit back in turn. You've got enough bounties to lock you down abroad for the next week assuming more aren't placed on you, so all it takes is something catching you before you can fly out and you're pretty much stuck in a loop unless you pay for a revive service. A service you might not get because you've proven yourself to be a rather unrepentant vault thief; very few people are going to trust you to pay up and not simply screw them over in turn.
I mean this as gently as I can be, but unless the negative attention and having your gameplay potentially disrupted for weeks to months at a time is the goal, you're not 'winning' by any tangible metric that matters.