IMO the easiest way to buy bitcoin is via coinbase (
http://www.coinbase.com).
My experience with it has been great -- it's essentially the same as starting a paypal account. Just make an account, link to your bank, and after you get linked (few days) hit just buy/sell however much bitcoin you want, and use it as a wallet without having to know much about bitcoin. Most people familiar with setting up any bank account would be at home with it. I think it'd be a great way to introduce someone new to it and make it not scary.
I have read repeatedly not to use an online wallet. That offline storage is the only secure way to store BTC. If BTC are vulnerable with online storage, then I doubt many people will be comfortable with online storage. What's the truth about BTC storage?
If you use an online wallet, you are trusting that:
a) The wallet provider will not steal your money
b) The wallet provider has good enough security measures so that a thief, or hacker will not steal your money
If you use an offline wallet, with a strong enough passphrase, you will be the only one who can access your money.
For this reason, I use an online wallet to store a small amount of BTC, enough for day-to-day transactions. I store the rest of my BTC offline.