Second, i think it was a combination of the flags of two primary land owners (Lord Baltimore and someone else)
The dates and pictures on the flags really help with guessing.
The best flag is New Mexico by a mile, although I suppose the Zia could be a little bigger.
I also really like Arizona. I think underrated flags are Hawaii, Ohio and Rhode Island, even Wyoming. You need something big, bold, easily recognizable, can be seen from a distance.
I do kind of like Virginia, because it's so gonzo.
The absolute worst flags? Wisconsin (1848!!!), South Dakota, North Dakota (not very good artistry at all), Nevada (so many lost opportunities, why isn't their flag the oro y plata one? Also, why does Idaho need to say "Idaho" two times on its flag?
if you have to put the name of what you are representing on the flag, you have failed