I recently (2 years ago) discovered Bitcoin and started researching and following it back then. The price was about $14 when I seriously considered buying some. The technology posed a bit of a hurdle in the learning curve, so here are a few thoughts on how to go about buying bitcoins, managing wallets, and spending your BTC.
First, I live in the USA. So transferring money from a bank account is pretty well supported on popular money sites (PayPal, Dwolla, Coinbase).
If you live outside the US, try a site like LocalBitcoins.com which has many ways to buy and sell Bitcoins person-to-person.
You will need to convert your USD into Bitcoins, this happens at an exchange, like BitStamp. You will need to connect a bank account (via ACH) to BitStamp in order to fund your account with dollars.
If you live in the US, Coinbase is very easy to use. You can buy BTC directly using your bank account. Then you can move them to whatever wallet you want. It is recommended you store your wallet on your computer and backup the wallet and private keys incase of a harddrive failure or someone steals your computer.
I bought coins on Coinbase, then transferred to my desktop wallet using the client MultiBit (Electrum is another good desktop wallet), which has a built in exchange rate calculator. You also do not have to download and sync the entire blockchain which can take upwards of 48-72 hours to complete the first time (using the reference Bitcoin-qt client).
For an online wallet I use Coinbase to buy coins. BitStamp to buy/sell for speculation and I have a mobile wallet I use on my iPhone hosted at blockchain.info. This makes it easy to pay for a cup of coffee or at a retailer that I come across who supports Bitcoin. I do not store many coins here, as I treat it like Cash in my traditional wallet. Only about $20 worth.