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I don't think Jishuku does translate. I think it would be written as 'Jishuku' with a footnote (or earlier explanation in the main text).
> 1. I wonder if "jishuku" needs to be capitalized.
Probably not. Although it you did translate jishuku as Self Restraint (with the capitals) and footnote that it would be an indication that Self Restraint is a specific thing here and not what you might typically be thinking.
> 2. I wonder if the idiom "fly in the face of" really fits this.
In the context of this sentence I think the ～～の波に乗らない metaphor is being used to emphasise his deliberate (and possibly a little shocking) breaking with convention / tradition.
I suppose you could use "bucked the convention/tradition of" as a translation, but that feels too blatant to me.
