Filing as a C-Corp? :) I'd be taxed twice. The LLC would have to pay income tax on its earnings then I'd have to pay taxes during the distribution to all the members (myself). This will be viewed as income tax. Definitely not. Though, filing as an S-Corp would take away the annoying/abusive self-employed tax of %15. Problem, again, the IRS... they hate S-Corps and they will make sure I fail to comply. My problem with filling as an S-Corp is that the LLC wouldn't pay self employment tax but the member would have to. So if I make $1 million, I withdraw $1 million (which is the goal), I'd pay the full self employment tax anyway. Does it make sense?
Last but not least, regarding your 1st point it all depends on your goals. I'm not rich and I'm still alive. Obviously I already know I can survive with $100 k/y not a problem. Now, majority of the people are looking for security first, then comfort and finally, they want to become rich. I personally want to become rich first. Then I'll be looking for comfort then security last. I'm looking for freedom, that's my main goal. We have different goals so we can't argue with each other on that specific point unfortunately. I view taxes as an obstacle... some don't which is fine.