Buy it for Life

I dont have a specific brand in mind per se mostly because in my experience the same brand will have several different boots with wildly different constructions and quality over even a years worth of manufacturing. There are brands that are more consistent than others but it pays to not buy strictly because of the name.

I'll be speaking mostly in terms of longevity but this can come with some tradeoffs that'll I'll get into in a second. Like I said above repairablity is really what will get you the longest wear out of your boots along with regular maintenance. The most repairable construction method will be a Goodyear-welted method this is where a strip of leather is sewn directly to both the insole and the upper where then a sole or midsole is glued and sewn to the bottom. All of those pieces can be replaced as long as the upper isn't too worn out. Tradeoff to a goodyear welt is that it can make the sole bulkier and heavier due to the extra architecture. Glued or differently sewn boot soles can be just fine for some folks but many of those boots severely limit what cobblers can do to bring the boots back.

To address your specific concerns, it doesn't seems like a fully waterproof boot is necessary just one that has a little bit of treatment. Well conditioned and waxed leather will be almost completely waterproof to begin with but you can go even further with things like silicone weatherproofing sprays which will also work fo synthetic materials. Ankle support will be provided by most boots that lace tigher above the ankle.

As for the fit, have you had someone fit a pair of boots to you before or has it been diy so far?