I've had an accountant do my taxes since I was 19, and feel like I've probably saved a pretty substantial amount of money --- not by doing elaborate things to structure my income (there are accounting tricks that do that, and I agree with you that exploiting them feels skeezy), but simply by ensuring I'm doing them correctly and, more importantly, on time.

Legal expenses are, as you say, a question of personality and risk tolerance. After we sold Matasano, I talked to people who'd been operating other large consultancies, and was shocked to learn that there are big firms that just sign every contract their clients give them. We got every contract reviewed, one by one, at significant expense. They just signed and started working. Our outcomes were comparable!

We still get everything reviewed at the new company. It costs money, but not so much that it changes the economics of the work, and I've had enough close calls over 20 years of working that it's worth it just not to worry. But reasonable people disagree about this all the time.

I do think you're wrong about the sole proprietorship thing, though. An LLC is extremely cheap (you don't even need a lawyer) and protects your personal assets from business liabilities. On the other hand, your legal strategy probably just involves fleeing the country to hide amongst the penguins along the 70th parallel.