There is no guarantee that you will ever reclaim any portion of your initial investment.  Be prepared to live with that fact before you continue.  Please read up on difficulty adjustments and estimated earnings before deciding if you can part with the money.

That said, pick a mining pool, fire up your video card and collect payouts to your wallet.  Transfer the coins to your favorite exchange and sell them.  Then you have to choose how to get the money out of the exchange.  If you're US based, dwolla is one option that most of the exchanges support.  I would recommend doing this in at least 1.0 BTC increments.

Entire process from payout from the pool to bank account will take about 3 days if you sell at market rates.  Expect to pay 0.7% (or less) to the exchange site and $0.25/transaction to Dwolla.

I can personally say yes, I've got cash in hand as a result of mining.