The thing is, the word means "Enter the owner's land or property without permission." Currently this does not require any skills and what trespassing allows you to do is actually more along the lines of snooping: "Investigate or look around furtively in an attempt to find out something, esp. information about someone's private affairs."
It's not uncommon for new people to the Seatribe games to be confused by this, and all it takes is simply renaming the skill. And for clarities sake, perhaps all characters should start with a "fake" skill called trespassing so they know it's something they can do if required.