So, am I missing something, or is Anaconda pilot the only one in the game without a Specialist skill? Or is this a bug in AB? If not, was there any explanation given on this? Also, the official PDF contains a note, NOTE: This unit is composed of one Anaconda TAG and one Operator. Does the operator start on the outside?
That's because the Anaconda Operator isn't a Pilot, and can't voluntarily dismount. You start with the Anaconda on the table, the Operator only appears once the Anaconda has taken enough damage to put it on 0 STR or less, see http://infinitythewiki.com/en/Evacuation_Device_(ED)#ED:_Escape_System One of the big differences to a Pilot is that the Operator is still a 'normal' trooper who generates Orders and is worth the full points cost of the unit, even after the Anaconda profile has been removed.
It's basically a balance/gameplay issue - Pilots got some extra toys due to being weak and very under-used, while Operators were already reasonably powerful and being 'automatically' in use if their TAG is fielded.
The Gorgos has broadly similar mechanics, but its inactive armor profile did get specialist operative. I guess the important point is that the Gorgos can voluntarily shed its armor, although it can't get back in.