Thanks so much for the kind welcome! Crazy to see this come full circle (LOL).

So I ran some simple blockchain analysis on Blockchair, I was looking for (and I believe someone in the thread suggested this) 1000 unique outputs holding exactly 5 BTC (that are still spendable) that were created between July 2014 and April 2015 (I arbitrarily figured these dates may be when WoodCarver would have issued his coins), and I got 630-ish results;
https://blockchair.com/bitcoin/outputs?s=value(desc),time(desc)&q=value(500000000),time(2014-07..2015-04),is_spent(false)#
This means he probably didn't create them during this time, or at least not all of them at once.

Then I ran the numbers back to January, now we have plenty of results, about 1300+ 5 BTC outputs that are still spendable.
https://blockchair.com/bitcoin/outputs?s=value(desc),time(desc)&q=value(500000000),time(2014-01..2015-04),is_spent(false)#

I think we can narrow these results to see if maybe a batch of 1000 was created at once, (via script) it seems that would be the way someone would generate 1000 addresses, or no? Or...in essence we're looking at the funding dates of the addresses, not the creation dates. so how would you think someone would fund 1000 addresses? At once? over time?