But with ONE simple rule, you have do it right from the start.
Do not use excahnge , because in with any notable amount you will have to submit ID or something .
My view is that if individual buys btc on localbitcoins or from a "BTC dealer " it is very hard to find out that he did .
Aren't you missing something in your suggestion? To wit, how on Earth are you going to get bitcoins in the first place unless you mine them? But mining is not available to everyone. So you will have to buy it somewhere, on exchange, localbitcoins or from a "BTC dealer". And buying coins from someone in person may not only be far from anonymous, it may in fact be quite dangerous.
If you want anonymity, you will have to provide fake personal information. But that would be illegal and probably considered an outright criminal activity once discovered.