I will be starting a Self-Directed Roth IRA very soon and I'm wondering what expenes might I occur. I would like to make monthly deductions from my checking account, but I'm questioning the expenes/fees from doing it contributing monthly or annually. Which is better?

There should not be any expenses which you will incur to simply contribute to an IRA. Most brokerages these days should be happy to take your monthly or annual check (or direct deposit) without a problem. What you do need to be concerned about is how often you will be buying or selling stocks, etc. Brokers charge a certain fee for each trade you make.

I know Waterhouse has something they call "Periodic Investing" where they let you add as little as $100 a month or a quarter and it is automatically adding to an existing mutual fund position (a mutual fund in which you already own some shares). They probably have a small fee associated with this plan. Other brokers may have similar deals. Call up some discount brokerage firms and find out what they can do!

Hope this helps!