Your theory is correct. I had some sort of clever justification for why that made sense in-universe but I forget what it was; the Doylist reason was that I wanted the red herring in this puzzle to be as simple as possible.
The original generation code is up here if you want to take a look.
(Good question, by the way; I added a note to the main post to clarify this.)
Yes to the first question.
To the second: you can aim to reduce repair costs with your interventions, but since they won’t come out of your budget that’s more of an optional extra for further impressing the brass.
That’s exactly right.
All your assumptions are correct, with the debatable exception of the last one: you have a record for every voyage
made along the same route you’re taking
by a supply ship
working for the same Navy as you
in the span 1396-1405.
Your interpretation is exactly correct.
I can confirm it’s not a mistake on my part. Beyond that, I leave it to you to decide what’s going on here and whether it’s relevant.
Good catch, edited now, tyvm.
I’m glad you got what I was going for. However, you should probably spoiler that meta-point, so people trying this challenge in the future can look for clarifications in the comments without being spoiled.
From your knowledge of wizardly adherence to habit, the way he never suggested getting items anywhere but the caravans, your knowledge of local markets, and the fact that everyone selling seems to recognize the Owle owl following you, you can be pretty sure that Wakalix bought all 836 of the items on his list from the same source(s) you’re currently considering.
(Regarding the other implications of your question, I neither confirm nor deny anything.)
Fun thought, but no. In fact, none of the available magic items can help you in that way.
Somehow forgot to link to dataset in OP, fixed now.