2016 Free Dining Watch ~ Part 2

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I currently have reservations for Aug 20-Aug 30 at Pop Century and am hoping to get the dining plan. I know there is no definite answer for whether it'll be Aug 14 or Aug 23 arrival date, but would it be possible to stay off Disney property for Aug 20-23, then get an Uber to Pop Century and stay from Aug 23-30? I know it'll only be 7 days for the dining plan, but that'll save my GF and I a good chunk of money since we have 8 TS ADR's booked.
 
How confident are we that it'll be on a landmark time (something ending in 00 or 30 (or 15 or 45))?
 
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