Not for us. If looking to maximize (or rather, minimize the amount of leave burned), for us, using a standard work-week as an example, the most optimal day to travel out is on a Monday, which probably doesn't bode well for upgrade chances. If we depart the local area on a Saturday or Sunday or non-duty, the day you depart the local area is considered a day of leave, regardless of what time of day you depart. The most optimal day to minimize leave burned is to return is on a Saturday, which may be better for upgrades, because if you return on a non-duty day, the day you return to the local area is not charged as leave. If you return on a Sunday, the Saturday is still charged as leave. Also, if leaving on a work-day, we can further optimize our leave because with commander approval, you can work a half-day and depart the local area in the afternoon, and that day is not charged as leave in anyway (we cannot take 1/2 days, even though we accrue leave at a rate of 2.5 days/month).

I have planned my leave around mileage redemption availability or maximizing leave but I've personally never planned my leave around complimentary upgrade chances though and I don't think I've even adjusted my dates around Upgrade Cert availability; only my routes and maybe my departure times, as long as the route/departure time with RUC availability still meets my schedule needs.