I fly this route 4 or 5 times a year. Most times I opt for the true redeye since that gives you a chance to go out for a nice dinner before getting to SFO. And while I do the 5PM often as well (I call it the pinkeye), it comes with a big risk. End of day delayed flights. And when the 5PM is delayed, usually 3 or 4 hours, that leads to landing at 3 or 4AM at IAD. And that is just brutal IMO, and I live just 5 minutes from the airport. As to equipment, it doesn't matter, they all stick and the planes will be full in back so you won't have any room. And you won't get an upgrade either, I am rarely upgraded on these as a 1k and I use my CPUs and GPUs to try and usually end up 5th or 6th on the list.