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There are many benefits to timing your practice, including:
It definitely gets faster as you go along. This was especially true for sections like activities, work experience and self-reported transcripts. The first time through is definitely the most difficult for those items. After that, it's a piece of cake.
As far as essays, you can recycle themes, but I found myself completely rewriting 80% of essays, even if they are mostly repeats.
My experience: after the first couple of apps, the work for the rest of the apps was restricted to:
1) Tackling the Why School aspect - obviously -.
2) Fidgeting with essay lengths when recycling.
3) Maybe writing 1 or 2 at the most new (usually short) essays to answer some question not asked before.