At some point you realise, exchanges don't let you withdraw large amounts and banks close your accounts at the mere mention of Bitcoin due to money laundering and liability concerns. Your money is locked into the system, allowing only a few trickles into your bank account.
But then again. Banks are digging their own graves. Can't get money out of the system? The system becomes the new money. All is a question of time.
The guy I buy from regularly on Localbitcoins had his fiat bank account shut down. Hes started a new one & created a bogus company so he can continue to trade.
Its not difficult to work around money laundering, we have two official businesses but I have 8 directorships. You just filter the money into/through as many companies as you can to reduce taxes.
Besides when bitcoin goes to the moon you wont want to cash it all out, youll be able to live on bitcoin (hopefully).
What you are describing actually *IS* money laundering (instead of a workaround). Risky business if you ask me.
Maybe I have misunderstood... otherwise that is NOT how I would do it...