The Dog Island (Wii)
For $3 used, and with recollections of someone at NWR swearing this game was quality even if it does look like a total overload of cuteness, I figured this was worth a shot. Worst case, I've got a spare Wii game case and my daughter will enjoy the game for long enough to get fair value from my $3. Best case I've grabbed a semi-hidden gem.
[Edit: Having now sat down and played with my daughter for an hour or so, this really is a great game for kids. Quality all around and near-terminal cuteness. Not much challenge and almost as much watching as actual playing... but that works to your advantage with young ones! Very pleased to have taken the chance on this one.]
After buying The Dog Island I didn't have quite enough left over to pick up Babysitting Mama (new, complete with baby) for $10... but that was sorely tempting. I still can't believe that game exists and want a copy for kitsch value alone. Maybe another day.