Hey man, I used to get paid to do that!

As far as redeeming 25K/35K (from Hawaii) miles on United, you wouldn't believe how creative I had to get. Since Saver seats are often very limited and inventory control usually doesn't replenish the supply right away, many of the favorable routes tend to be sold out.

I once had to route a lady from HNL-LAX-PDX-DEN-DRO for her outbound, then for her return she went DRO-DEN-ORD-LAX-HNL...just so she could use her 35K.