[dragonwriter]

Yeah, did something similar with an actual colonial (18th Century) apprentice's indenture, with similar results. It did, however, flag some provisions as potentially legally problematic, so it clearly has some remote idea that there are legal limits on contracts. Specifically, it called out in the "Standard Practice Comparison":

"Prohibitions on Personal Activities The contract restricts personal activities like marrying and playing unlawful games. Today, such personal prohibitions would likely be deemed overly restrictive and unacceptable under employment law."

(OTOH, while recognizing that employment law was relevant, it didn't call out that the consideration from the employer for the 5-year employment period didn't include any financial compensation was both far out of standard practice, contrary to employment law, and, if you ignore the invalidity the way the AI apparently does, a pretty big thing the apprentice should take note of, noting instead that the room and board commitment was a big plus, so not giving it much credit here.)

[dragonwriter]

Also, I tried the same identure contract from the other side (the master rather than the apprentice) and, some highights of the comparison:

(1) the room and board commitment that it called out as a plus as a clear commitment for the apprentice side, it called out as a negative as excessively vague for the apprentice.

(2) The "Standard Practice Comparison" calls out the 5-year term and associated commitments as standard to the Master, while calling them out as unusually burdensome and out of line with standards for the Apprentice.

(3) the "Recommendations" on the Master's side (reproduced below) are actually written as recommendations to the Apprentice. Giving the recommendations for the wrong party is a pretty big failure, even if everything else was right.

  Recommendations

  Follow the Rules

  Make sure to do what the contract says. Follow your Master's lawful commands and don't break the rules, like playing illegal games or skipping work.

  Protect the Business

  Keep your Master's secrets and don't let anyone damage their business. If you see something wrong, you should tell your Master.

  Respect Boundaries
  
  Don’t get married or waste your Master’s things during your apprenticeship. Focus on your learning and duties.

  Stay Committed

  You agreed to work for five years. Stick with it unless your Master says it's okay to leave.

  Learn Well

  Take the chance to learn as much as you can from your Master about being a merchant. It's a big part of the deal.