Proper pre-trip conditioning, pace, hydration, and pressure breathing help alot with regards to preventing AMS.
Spending a night at Horseshoe Meadows will help also.
Amen, Tim. Time was, drugs were used primarily to help get climbers down from mountains if they found themselves in trouble. Now people seem to be using drugs as crutches. Dexamethasone has become an epidemic within high altitude climbing. Sure, Diamox can help your body to acclimitize faster than it otherwise might. But so can proper physical conditioning and good hydration.
Mattncl, the best way to increase your chances of reaching the summit is to get in shape. You're gonna do Kili? And my answer to your original question is: No, your itinerary doesn't really sound reasonable. I live on the eastern seaboard also, and if you're coming from Boston, your acclimatization plan sounds insufficient to me, particularly if you've never been on a 14er before. If I were you, I would spend AT LEAST 2 nights at Portal, spending the day in between hiking at an elevation of 10,000 ft.+
Acclimatization is particularly important if you've never been on a 14er before -- can't stress this enough. There's just no substitute for acclimatization. No drug is going to get you to the top.
