Thistle, 2 MAY be the more practical choice. But let me tell you my own thinking.
Your climate might be similar to mine. We have four main seasons. In truth, we also have 2 more mini-bridge seasons....late-winter-early-spring (when you really need winter warmth still but the light seems to demand spring colours) and late-summer-early-fall (when the temps are still very warm but the light is beginning to fade and you yearn for richer colours.)
I actually have VERY few clothes that span all my seasons. It's just not possible. The light linens I wear in true summer have no place in my winter closet. The wools and cashmeres that I need in winter are downright ridiculous, not only in a good portion of my spring and fall.
Yes, there are one or two polyester jersey dresses (like your green one in the other post) that I manage to wear year round -- particularly if I am going to be someplace air conditioned (which in my case, isn't all that often).
But for the most part, I trade items out. So, that means I have items that I mostly wear in 6 - 8 week blocks, then trading them out for others.
The warm winter dress that I wear from late November through late February gets traded for the lighter weight dress. And that lighter weight dress in turn gets traded, come summer, for something lighter still.
The cross seasonal dresses stay in the closet, but the others rotate.
Now, I admit, this means I have a lot less variety within any one 6-8 week block. But for some reason that doesn't bother me too much. Because when I switch up the closet, it's like I've got half a new wardrobe and I get to try out new combinations.
I do my switching purely by the weather. If it starts getting warm earlier, out come the "spring" things. If it's still cold, I keep with the winters.
I do this mainly with dresses and toppers, by the way, as well as a few of my pants.
It might be easier for me, however, because I work from home and my outings take me to different settings.
