sunshine_eggo
Victron's little biatch
Yes, I have already mentioned on the forum that I am completely new to solar and have only taken in interest in it in the last few months. So I fully acknowledge that I have little understanding of how PV works. That is why I was asking questions about how many bare wires I could cram into a Victron charge controller.
On one side you acknowledge your own ignorance, yet on the other side, you think you know enough to put forth something similar to: "surely somebody has figured this thing out by now, it's easy/simple."
You're forming opinions and approaching design using expertise you don't have.
You're also making design decisions based on what YOU think is best rather than those with experience... including the manufacturers.
The easy/simple thing is to do it right rather than try to come up with some janky and potentially unreliable solution.
5S6P requires ZERO intervention on your part. EVER. The only time it ever matters is the day you connect the array - just don't hook it up backwards. Done.
The key word here being "majority" of their rated voltage. Shouldn't we also take into account line losses (perhaps ~3%)
Again, this is where your ignorance manifests. There are ZERO line losses at Voc. For there to be losses, current MUST flow. If no current is flowing, you get 100% of Voc.
on an array totaling 223.32 VOC, that would amount to a decrease of 6.7 volts, no? That would bring the array down to 216.62 volts, which allows for a nice 15% margin before hitting the 250 V figure.
As line losses don't happen, the above is irrelevant.
In any case, I think some are missing the point. I could theoretically run 30 panels (6S5P) with the 250/100 without any issue for probably at least the next 7 or 8 months, and not have to worry about any possibility of extreme cold weather. That gives me plenty of time to find a bargain on another charge controller if I decide to go that route, and plenty of time to re-configure my strings/array before winter cold arrives.
The point is you are a self-admitted newb making a poor design choice, and are actively resisting the advice of those with greater experience than you INCLUDING the manufacturers, the NEC, etc.
As I already said before, the reason for paralleling multiple strings is because I expect to not have all the panels facing the sun at the same time, and there are time when certain groups of panels are partially shaded during the day.
Which is stronger argument for 5S6P vs. 6S5P.
So, I expect when you take into account *ALL* the factors, such as line losses, shading, not all panels facing the same direction hitting the sun at the same time,
The above have no/little influence.
the fact that coldest temps in my area are most often *overnight* temps when it is DARK, and there is no light on the panels, and by the time the sun comes up, and a significant amount of light hits the panels, it typically warms up above freezing,
Have you actually confirmed this with data? The coldest time of any 24 hour period is usually the instant before dawn.
This is my weather station 10 day forecast:

These lows are within minutes of each day's sunrise. They occur when it transitions from a shaded to a white background - sunrise.
Your climate may vary, but the above is fairly typical.
I think I just might be okay
This sounds REALLY confident.
staying under 250 V with 6 in series, except for the occasional situation perhaps a few days per year, when it might stay cold and clear in the 20s all day long. That is a cross that bridge when you come to it kind of thing.
No. It's an active decision to make a bad design. Period. Those with more experience, the manufacturer, AND the NEC are saying:
"don't do this"
You're saying:
"I know better. I'm doing this anyway"
I have several months to learn and experiment and measure the panel voltages before it will get cold enough to have to worry about it.
IMHO, you have not demonstrated an actual willingness to learn. Good luck.