[Zidewinder]

If you want to keep things simple and maintain your privacy, you should check out services like BitQuick (http://www.bitquick.co) and Blue Sky Traders (http://ok2yri46aaptiu2d.onion). These services allow you to buy bitcoins by simply depositing cash into someone else's bank account. No ID required or anything. There's another similar service called http://www.cashintocoins.com, but I don't have any experience with them and they're apparently having issues with their SSL certificate right now.

Even if you do want to use an exchange in order to rapidly trade your coins and profit from price dips, depositing coins into an exchange is a lot easier and possibly more anonymous than depositing dollars.

Then if you decide to sell the coins, you can move them off the exchange and offer them on localbitcoins.com for physical cash.