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I like David, Ross and Gerard very much and Walter somewhat. I deplore Madison in all contexts, so I'd use Ross Madison and keep it hidden. Then your first three combos would be fine. Ceallach is outside my experience, and I imagine it would morph into the trite Kelly very quickly. Olaf Ceallach would please me more. Dexter is all cattle to me, and seems incongruous with Ivan - which is anyway my least favourite form of John. I'd use Iain Dexter if at all.

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A sibset of David, Ross, Gerard, Olaf and Iain (or Ian) would be good.