I've tried (and loved/hated) almost every style and brand of boot over the years, and I'm down to just two that I'm sticking with, each for a different purpose:
1. For most hiking, scouting, or hunting I wear Salomon trail runners. Super lightweight, great grip, and I'm not tired at the end of the day. The ones I have aren't sold as "waterproof," but they're much drier than others that I've had that claim to be. If it's not extreme enough for gaiters, I'm wearing these. I've waded through snow drifts and shallow creeks with them and stayed drier (and warmer) than anything else I've tried. These also have those new "speed laces" some shoes come with, so I can just slide them on without tying anything.
2. If the situation calls for gaiters, I go straight to my Muck boots. They're not ideal for 10 mile hikes, but I've gone 3-4 miles in them without blisters. They're heavier than a hiking boot, but NOTHING is getting inside them and I don't have to worry about my gaiters snagging on something. And again, there are no laces to tie.
I've gotten away from the traditional "boot" for another reason as well. I'm in Colorado and am often hunting in areas with mixed sage/juniper or near treelines. A lot of the time I find myself "squatting", trying to get low behind cover like sage bushes or pine blow-down near the edge of a meadow. Any boot will let you do that, but after 5 minutes, half/full-height boots get super uncomfortable for me. The trail runners just don't press on your ankles at all, while the Muck boots are so sloppy and flexible that it's not a problem. They're just more comfortable for me for what I do.
There's also some laziness involved. I get sweaty feet even in cold weather and even expensive Gore-Tex boots don't keep me dry. I love that both options let me slide off my footwear while I'm taking a rest, let my feet air out, and still be back on in 5 seconds if need be.