What does your common sense tell you? There are a lot of things that can be complex with watchmaking, but this isn't one of them.
My common sense is not the issue here; it's what I thought was a simple watchmaking question.
I recall, from one of your posts actually (that will be accurate, the recollection may not be...), that as the mainspring winds down, the watch has less power, therefore it's more difficult for it to be accurate. My question about winding time of day, each day, is relative to my understanding of this concept. With the little I know, I would wind my watch at about the same time each day. Easier to remember when to do it, and I would guess, would keep the mainspring at a higher state of wind, thus potentially improving timekeeping. If this is incorrect, please let me know.
But, for a new person, they may not understand this, and think, okay, once per day is inclusive of any time within the next day (or 24 hour) period. So this is where I thought the question was simple: from a technical point of view, does it matter for anything regarding timekeeping when the watch is re-wound the next day? It's either yes, or no. You either know the answer, or you don't. I realize this whole thread would be frustrating for you and I will apologize in advance, because my small, tangential question was not meant to add to that.