Thanks for the replies - I'm especially glad to know that generally, a request for freeplay in lieu of travel reimbursement is going to be viewed as easier to work around than actual travel reimbursement. I kind of get why, but from where I'm standing, they're both 'hard cash' costs and it doesn't much matter to me how it's handled. Actually, thanks to Amtrak points, it's usually significantly cheaper to use award tickets - I'd rather have freeplay to add to the bankroll.

As for junket flights, they worked well for me back in the day, but my dad is significantly more comfortable on a train than a plane. It might be feasible for the New Orleans trips (that's an asinine trip by train from Florida) but otherwise planes are pretty much out unless he can lay down.