Alex, as Discomatt said, we began our trip at Pinaroo. 2 guys who met us began further north as you are planning and said it was 'nothing exciting' north of Pinaroo. If you did start the trip at Pinaroo, allow 2 days to get to to Robe. You can do the Pinarro/Bordertown section in one day, but is best to have a overnight stop at Red Bluff Campground. From there will be a reasonably big day to get to Robe, but easily doable. Personally, I would consider Beachport or Southend ahead of Robe, but we all have differing opinions of what is better. I am heading back to Southend in February, much quieter than both Beachport and Robe, but not too far to drive to either to have a look around. Not sure if you saw it, but there are some pics and trip report from our trip on the Border Track last April in the trip section somewhere.
Remember Border track is closed from November to April if memory serves me correctly.
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