Disconnected Checkout - Best practices?

We use Vault 1.2.2 for our small dev team here at work.  It is a huge improvement from the constant frustrations that we faced with VSS over the years.  However, I have lately become so frustrated with the Disconnected Checkout (or Work Offline?) feature as to find it unusable and can no longer feel confident that any work I perform over the weekend will make it into my source control at the office.
 
It is likely that I am doing something wrong, so rather than give gory details about each step that I am doing (which I will gladly do), I would love for someone (at SourceGear or otherwise) to run through the steps that are required in a disconnected check-out scenario.  Then, (and this is the critical part) what are the steps to properly re-connect to the Vault on Monday morning without losing all your inspired weekend code.  That is the weak link for me right now, I keep losing everything when I come in on monday morning.  I hate to say it, but never had trouble with this feature of VSS, so I'm sure that I'm just doing it wrong with Vault.  Thanks for any help!
 
Josh