Just looking for tips on initializing conversation

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Let's say I'm taking my little dogs for a walk. As I'm walking a woman is walking the opposite direction towards me. Normally, as we pass each other, I'd nod my head and say "Hi", or say something like, "How's it going?" and that would be it. What are some better options to actually get a conversation going?

In situations like that, sometimes the brief interaction you describe is all the other party wants.

In those cases nothing you say is likely to spark further conversation, and if it does it likely will be viewed as awkward in hindsight.

Not that I know how to pick up on if more discussion might be awkward, I'm a deeply awkward person so all I can do is accept that.

If she herself also happens to be walking one or more dogs, you can talk about dogs, and perhaps pet each other's dogs.

(Hopefully your and her dogs won't instantly hate each other. But, if they do, then perhaps getting both your and her dogs to behave themselves could be turned into a shared project, around which you could establish some camaraderie.)

Other possibilities, especially if she doesn't have a dog:

If she happens to be wearing an item of clothing (such as a T-shirt) and/or jewelry that is relevant to some topic you are interested in (such as religious jewelry, if you happen to be religious), compliment her on that, and then perhaps make other relevant comments and/or ask relevant questions. For example, if you and she turn out to be adherents of the same religion, you can tell her which church (or other house of worship) you attend, and then ask her which church (or other house of worship) she attends.

More generally, look for evidence of any points of commonality, and use those as conversation pieces.

You yourself should make a point of wearing or carrying things that could be used as conversation pieces if another person happens to notice and comment on them.

Do NOT ask her where she lives. One of the surest ways to creep a woman out is to ask her where she lives. You can tell her where YOU live, however, and you can make comments about the neighborhood you both happen to be walking through at the moment.

With the majority of women you meet, there probably won't be any obvious points of commonality. This means that conversation beyond basic small talk won't be possible with the majority of women you meet. That's just a reality you'll have to accept.

P.S. to the above:

As a general rule (to which there are occasional exceptions), random meetings on the street are not the best way to meet potential romantic partners. In all likelihood, a woman you meet randomly on the street will be in a hurry to get somewhere, and will not have much time to talk to you even if there are some obvious points of commonality.

Also, another instant creep-out question to avoid asking: "Do you live alone?"