All great answers here. The one thing not mentioned is to consider carrying your overnight gear only to Outpost Camp at 10,400 elevation. You would sleep better, so would be more rested. Also carrying the gear only to that elevation takes way less energy. Then start early on summit day.
Or even consider the above, and then moving up to Trail Camp the second day, and doing the summit on day 3. This plan would likely be the surest way for you to make the summit. Note that if you have an overnight permit, there is no limit on the number of nites you stay out.
Regarding Diamox, since you have a history of AMS, you should definitely use it, and take it first the night before you climb to 10k elevation. Also, only take 125 mg or just half of that, twice a day. Make sure the doctor didn't prescribe the 250 mg pills.
