About six months ago, Completionator used to show me Est. Value for all my games, even if I had not set the New/Used status of the game.

Now it seems that none of my games' Est. Value is showing, unless I explicitly choose New or Used for a game.

1) Is this the correct behavior?
2) Is there a way to easily default all selected games to Used (and not have to fill in box/manual information)?

The site refreshes pricing data nightly, but sometimes there are issues. I think you just happened to catch it on one of those days. If memory serves, you do not need to select New or Used. If an item is set to Unassigned, it will use the "Loose" value since that's (generally) the lowest. We do not have any default or bulk edit options regarding the condition fields, though technically you don't need to do anything with the various box / manual type checkboxes. The site does factor them in when choosing CIB or Loose prices, but the actual conditions you enter do not matter.