Hi fpatten1509,
Beyond the significant expense associated with potentially taking the GMAT 8 times, the biggest 'flaw' in that plan is that you can only take the GMAT 5 times in a rolling 12-month period. For example, with the 16-day wait period, you could conceivably take the GMAT 5 times in a 2 month period... but then you would have to wait another 10 months until your first score fell outside the 12-month "window" before you could take the GMAT for the 6th time. So what would you do during those 10 months? Continue in full-on study mode, even though you wouldn't be able to take the GMAT for another 10 months? Stop studying and then start back up later (with the hope that your skills haven't gotten "too rusty")? Neither situation sounds particular efficient.
GMAT assassins aren't born, they're made,
Rich