1. Merrell moab hiking boots. Great, just not waterproof. Indeed, they wet through if I walk through heavy dew, which I do extremely frequently (daily, when I'm going hard birding in warmer weather). Didn't have to break them in, I love Merrell. Good condition.
2. Xtratuf rainboots. Fell apart within a few months catastrophically - cracks from ordinary walking that ran completely through the material which made them not waterproof. Threw them away. So sad because they were very easy to get on, very comfortable, and a fun rubber-ducky yellow.
3. Rubber boots from Hunter. Pretty OK condition but about 20% they're fine, 80% they make my feet hurt so much I cannot walk. Can't really break them in because rubber doesn't, and it's been more than a year of wearing them on and off. Almost got frostbite in them once despite wearing heavy socks and those toe warmer pads. The outside is flawless though and they are a gorgeous red colour, and being rubber they are waterproof.
4. Bean boots (unlined) in the classic rubber lower, leather upper. I just bought these. So far breaking in nicely. Kind of tough to get them on but it's improving/I'm getting better at it. The tongue is fully sewn to the upper (for waterproofing), so it can't swing fully out, and it doubles over where it's sewn, but I'm not actually getting any pain when walking around in them. I think I trust them enough to go on a few hours' hiking now.

And now since it's winter I really want another pair of lined/fleece boots. I've managed to get by, good lord, the past decade or more without snow boots, because I feel like it just doesn't snow much since I moved east. I almost never have to step over snow drifts or break trails, and I just wear sneakers. But I spend a lot of time outside and every year or so I do have an occasional outdoor day that IS very cold on the feet, and I have to flee when I feel frostbite setting in...