I checked the weather quite often that week and knew it was good enough for an afternoon summit, so I considered sleeping in a hotel in Lone Pine Friday night and starting at 7 AM. But I decided against it because I thought that staying in the Portal would be better for acclimation.
Looking back at it, I still don't know whether staying in Lone Pine would have been better. I would definitely have gotten much better sleep, but would staying at 3700' cause me to lose some of the acclimation I got in Mammoth?
I’m not sure how quickly altitude acclimation is lost with time. But I can say that spending a night at 3700ft would not have helped matters. In any case, what I think would have been better is camping at the Portal and getting a later start. I think that WAYYYYY too many people get into that mindset that getting a super dooper early start is the ONLY way to safely climb Whitney (and many other summits) ever. This in and of itself can make the hike both less safe and enjoyable by essentially making you hike as a zombie.
I DO agree with others here that TRAINING was probably a bigger issue than sleep. Regardless of what you decide to do in terms of sleeping arrangement or start time, it would probably be a good idea to get in some decent training hikes before attempting Whitney again. You already made it to Trail Crest with basically nothing. The summit is virtually guaranteed if you properly train for it. Consider your summit attempt to be your forst serious training hike!