Nope, don't travel at inconvenient times at all, the extent of my "optimization" is to check KVS to pick the most likely flight for an upgrade if there is a choice of a few that would work. Vast majority of travel is business-related, lots of tickets booked <7 days but still a lot of cheaper fares also.

There are some routes where I have almost 100% upgrade success - EWR-MDW/ORD being one of them. This is probably one of my most frequent routes. MDW flights are particularly good, usually upgraded 5 days out.