Stockwell, the advantage of strap-on crampons is that they'll fit any boot. (The disadvantage is that you spend more time tightening the straps if you want to get a really good fit that won't work itself loose. Imagine strapping yourself onto a pair of skis, vs step-in bindings.)
It's harder to get a good crampon fit with leather workboots, for a few reasons:
1) they don't have any built-in welts designed for hybrid or step-in crampons. If you're lucky, the gap between the sole and the leather will be enough to hold a hybrid crampon. (But if the boots aren't properly sewn and glued, you may end up prying the sole right off.)
2) The soles flex. This makes them comfortable for walking, but it also means that a step-in crampon will pop right off under stress. A hybrid probably will too, I haven't tried it.
3) The soles aren't quite the "right" shape. In particular, the soles tend to be wider than the boot itself, which most crampons aren't really designed for. If your crampon has metal attachment points, you may have to bend them a little for the best fit.
In short, workboots ==> strap-on crampons. In my experience, if I'm not seeking out ice, the light weight and comfort of the workboots are well worth the infrequent hassle of tightening straps when I need crampons. (If conditions are slippery but not very steep or icy, I wear Katoohla MicroSpikes, which are no hassle at all, but I usually carry crampons in my pack just in case.)
In conditions where you need crampons, hybrids or step-ins are convenient and secure - but require a stiffer, heavier boot. It's a pick-your-poison kind of situation. If you'd said you want to go ice climbing soon, I'd tell you to start with Trangos and hybrids and get used to a less comfortable boot. But it sounds like you're basically hiking, just in winter (or what Californians call winter). For that, I'd stick with comfortable boots as long as possible. Get out there and practice your self-arrest technique and your winter awareness generally (like recognizing early signs of frostbite and hypothermia), and don't worry too much about your boots.