ticket for the other friend. The problem is... what do I do with the
mid-November tickets? They cost about $230.00. To change one of them
to the beginning of October would result in a $250.00 change fee. ie.
it'd probably be cheaper for me just to buy new tickets.

Really? The change fee is usually more like $100. What's the city pair
and date and fare, so we can look up the actual rules?