Originally Posted by
787fan
my rule of thumb is that any domestic itinerary more than $600 a.i. or more than 13cpm should probably use miles to redeem
This is sound advice. However, if OP is on someone else's dime, and is up for a small risk, he should try the nesting/overlapping itinerary trick and maybe even incorporate a hidden-city segment if the ticket(s) is/are cheap enough.