SKARDAVNELNATE: Okay, I got it, but I'm not sure how.
Started a new game. Peeping Tom was the only achievement I was missing. Left the sensor plugged in. Looked at all the coordinates in the telescope. Still didn't have it.
Removed the sensor. Visited the junkyard. Visited the robot. Visited the device. Went to get the rag. Still didn't have it.
Plugged the sensor back in to the interface. Removed it again. Opened the datapouch and clicked when the cursor was a question mark. Went up to the roof from the deck. Went back to the deck through the inside. Went back to the roof through the inside. Now I had the achievement.
The achievements were added in a very last-minute capacity, I believe by Wadjet Eye as opposed to by the coder on Primordia, which may explain why their behavior is so odd, since the main coder's style was a bit idiosyncratic and it's possible WEG couldn't quite figure it out.