At what point in the scenario(s) did the bank lend out more than its cash reserves in a single transaction?
At the point where it approved a $1000 loan to me to build a boat, which created a $1000 draw-down account for me, despite only having $100 cash on hand.
In this scenario, printing and handing out cashier's checks is essentially printing money.
No. There's a fundamental difference; the bank doesn't have to redeem money, but does need to redeem cashier's checks.
At the end of paying back the loans used to build the boat the bank has $100 and owes $1000. Please show me where the bank's spare $200 is.
In deposits of the bank. It received $1200 in deposits from me and used $1000 of them to retire $1000 in liabilities. It also has a total of $1000 in depository receipts and a corresponding liability of $1000. Don't confuse "money" with "currency"; money on deposit in the bank is still money.