Real life isnt a Hollywood movie with good cop ending. No it wont if you are clever enough.
That being said i am sure Bitcoin is enough for your needs.
Using Bitcoin wanting to protect your stash from prying is a real pain because you have to take extra precautions and use other services, while with Monero you can just have one address and use different levels of mixing when sending transactions to match the level of privacy you would like to ensure, this is what bitcoin had to be since day one, but they got most of the people saying its a plus for accountability, and it really is and thats why I think bitcoin and monero will co-exist.
good question lol, and in the scenario you get rich from XMR, it will for sure be accepted in lots of places so in the ideal world you trade services directly with xmr, otherwise you'll have to deal with xmr->btc or even xmr->btc->cash transactions.
absolutely, no one will ever know the size of your original xmr stash, only possible to know is what was converted to btc and/or cash.
This all depends (right now at least) what country you plan on cashing out on - for example, as a us citizen, i'd have to pay major capitol gains on taxes to explain how i got so rich and moved to mexico.
Right now, in this early stage, EVERY country has differnet btc rules/laws. you can't just say oh i can cash out my xmr tomorrow on whatever exchange and get rich anonymously. where is the brain behind that idea again? sorry, just being real, cuz this seems kinda out there to me, other than the protocol and design, but still it won't help you cash out btc in the uSA right now.. just sayin.... :\
EDIT / TL;DR - i understand the whitepaper, i'm a nerd. what I don't understand is people assuming they can cash it all out on btc anonymously. thx!