Is it smart to optimize your personalized plan throughout the day or just once right when you arrive?
I think this is a personal choice. If you are a flexible person who can change directions easily, then optimizing a couple of times as you go along should save you a few minutes here and there. I am not that kind of person. 
I like to have a plan and stick to the plan even if the plan is a bit less efficient.
Of course if things get really off, like if you arrive at a completely different time than expected, or if the first few wait times are very different then predicted, then optimizing is your best chance to adjust.
I have re-optimized in the park a few times but then I feel like I am spending more time sucked into my phone crunching minutes of my touring plan and missing out on the fun & magic around me.
I also like knowing my plans too & re-optimizing can really throw a wrench in that, so if we start to fall behind we just start skipping things. I have also learned that setting my pace to relaxed really helps us stay more on track. Also I’ve learned that for my family, planning my first 2 days and leaving the rest as “clean-up” days to pick up what was missed the first 2 days is really a nice way to plan.
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My strategy is to only re-optimize if I am going significantly off schedule.