Vanguard's customer service is usually quite helpful, as long as you can get through the hold. Also check out their website. at http://personal.vanguard.com/Is there any advantage in going with this over investing in SPY? A few: lower broker fees (only $20 a year for low-balance investors; you're currently paying $48)- no bid-ask spread when you transactThere may also be disadvantages. As a mutual fund, the terms of it are set up to protect the shareholders in aggregate, but these same terms could also be used to screw individuals.1) Can you have automatic monthly debits invested into a Vanguard fund?Yes; you have to fill out certain areas of the application forms to activate this2) If so, is there a fee/commission to do this, and how much?None beyond the "custodial fee" ($10/yr) and "account maintenance fee" ($10/yr) which apply to everybody and which go away when your balance gets large enough.3) What would be the process for moving my current investment out of Sharebuilder and into a Vanguard fund? Call vanguard (or visit their website) and ask them to send you the IRA application kit. In the kit there will be a form letter for account transfers with some blank spots; you fill in your account information at sharebuilder. There are a few check boxes; you want to direct them to liquidate the account and transfer the proceeds in cash to Vanguard. Sharebuilder will charge you some fees to do this (looks like $15.95 for executing the sell, $50 for the account transfer out; check with them to be sure). You may wish to calculate exactly how long it will take for you to make back the $66 in fees. My estimate is two years.