I have several pairs of Kenetreks of different types, and they're outstanding boots. That said, I wear them much less now than I used to - they've become gear almost exclusively for very cold-weather/snow, extremely rugged, steep terrain, or if I expect to not be doing much walking. The reason for this is their weight - they're tanks, and last a long, long time, but they're heavy. And every pound on your feet burns the energy of carrying about 7lbs on your back. If it's not snow, extreme cold, or extremely rugged/rocky terrain, I go with Salomon Quest 4s. They're light, pretty rugged, and very comfortable for me.
Given what you've shared, and are looking for late-season/cold weather boots, the Kenetreks would be a great choice for your cold-weather situations. And because of that, I'd recommend the insulated boots. If you already have a pair of non-insulated, the insulated would help round-out your gear.