Thanks for the input.

I would do it at the time of booking but sometimes it is something that I don't know until the date gets closer. I often don't have a full schedule until a week before an event.

For example, this weekend I am FWA to DTW to DCA getting in around 5p.

I thought we were going to meet up that evening but it turns out we don't do anything until the next day. So I have all evening to add a leg or two in there.

For SDC, is the easiest way to do that from the counter at the airport? on the phone? is there a way to do it online?

What about going to DTW and going to the Sky Club to get them to re-route me for more miles?

Note: I have checked baggage.