I agree. Very complicated. But fortunately, a state structure already exists.
Your county by county model would either operate for the entire US, or not at all. Counties are too small to be a viable country. The vast majority of cities are Democrat so would demand independence. So you might damage your own ideal using that model. I think it's a state by state thing. Smaller than that is impractical.
As you say, CAC (California and Cascadia, plus Hawaii and Nevada) would have to absorb a per capita portion of the debt, split military assets etc. I think CAC is easily big enough to stand on its own two feet. And with the Central Valley, grow its own food. It wouldn't need to hook up with Mexico or Canada.
Also no reason not to trade with the Trump rump of the USA, but CAC would organise itself the way it wants to, which isn't the way the folks in the middle approach things.
I imagine Newland (New England, New Jersey and New York) would split off if CAC does. Maryland and Virginia too. A few more years and we may see Arizona, New Mexico and Colorado join CAC. But sadly, not Idaho, in spite of its beauty.
All told, the US would lose about half of its population. The other half could then happily enjoy its tax-free, gun-lovin' anarchy and launch wars with Iran. That kind of stuff. The good news is that Mexicans will pay for Trump's wall to keep you guys in.