Rob, as an avid tinkerer/modder I have a tear of admiration for you in my eyes as I write this, however I don't think that using jungles as an all-season boot is the best solution.
With the phasing out of the black boots for all US services, you'll find some awesome deals on surplus temperate boots. It just so happens that the most recent temperate boot, the ICB (Infantry Combat Boot), is goretex lined. I know these boots well, because they are what I use. I also know that when I was overseas, I was able to pick up a few pairs of brand new black Wellco and Belleville ICBs for under US$80 shipped airmail to a place that is hotter than here (no, not the desert). Stateside you'd be looking at under $50 shipped for a brand new pair.
Run a search on ebay for "ICB", "Infantry Combat Boot", "Wellco", "Bates" or "Belleville" and look at their surplus listings. You'll be pleasantly surprised at some of the prices you see. The tan "ACU" boots are the same, but you'll pay extra for them because they are current cool-guy gear.
So how do the ICBs go out in the booneys? Very well. They are not quite as tough as the Caddilacs or jungles, but they are 100 times more comfortable and they are fully waterproof. I have been wearing a pair of ICBs for over two years now - daily wear - and the only problem I have found is that the sole is wearing. I have used them in desert, temperate, tropical jungle and concrete jungle. All with zero failures.
Go for the surplus US issue ICBs.
Smudge has some good ideas for boots above - Danners, Matterhorns, etc. But STAY AWAY from Hi-tec Magnums. They are nowhere near as tough as they used to be since they moved manufacturing to china and they WILL FAIL ON YOU.