I'm a little intimidated at the prospect of joining an exchange (looks like I'll have to go through two or three middle men before I can actually get any money in) and I don't intend on day trading or speculating, so I was thinking about using prepaid debit cards on get-bitcoin.com.
Any advice?
If you use one of the exchanges you will always get a better price. If you are not buying/selling regularly you may not care about this so it is up to you to decide.
Regarding the "best place to buy", any of the top exchanges are good. I vote for
CampBX. They have excellent support and a nice interface to buy/sell coins.