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Is it ever appropriate to "leave out" affiliation with an organization, or employment with an advocacy group, or something like that - if it is a clear-cut signal of political ideology?

I've certainly left out organization affiliations; but I'm concerned about the employment-side of things because that leaves resume gaps. I'm not embarrassed about my associations, I just don't think they have anything to do with my work as an attorney - and I want to ensure that the decision making process on my applications is neutral re this also.

Not a problem at all.

Sure. Resume gaps are usually overrated. Nobody ever notices them.

I can't leave out prior political affiliations from my resume because it's a significant portion of my college work experience. Although I do have 2+ years of post-college work experience, I have good, team-leadership things to say from my political experience so I really want it in there.

Interviewers ask me about it about 50% of the time. Some seem excited about my previous affiliation and say so. None have ever said anything negative to me, although I'm sure many have thought it. But tactfully avoiding touchy political issues in an interview and finding a way to refocus the light on something that most people agree on is a social skill--and is another thing that you can put on display in your interview. If you have good skills to demonstrate by your political experience, leave it on.