Might be worth considering a boot that's more than a hiking boot but less than a mountaineering boot, like the Scarpa Zodiac Tech:
https://www.scarpa.com/zodiac-tech-gtx. They are advertised as a lightly insulated 3-season boot, but in my experience they hold their own just fine during winter in CO. Semi-auto crampon compatible, warm, and way more comfortable on the trail than a full blown mountaineering boot.
In the meantime, I think your Quests with thick merino wool socks will be just fine for something like Quandary. Get yourself a set of Katahoola Microspikes, as well as some gaiters (like the BD Front Point) and you should be set. A fresh coat of Nikwax on those might not be a bad idea heading into winter (I have to do it to my Quests at least 2x per year or the leather wets out in the snow).