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I think the name would be pronounced as /ˈɡwɛnwɨ̞nwɨ̞n/ in the North of Wales, and /ˈɡweːnʊi̯nʊi̯n/, /ˈɡwɛnʊi̯nʊi̯n/, or /ˈɡwɛnwɪnwɪn/ in the South, but given that it's such an unusual name, I don't think I can verify this at all easily.
Looking at potential meanings for this name based off of the roots, I have to conclude that Gwenwynwyn ab Owain Cyfeiliog's parents were either very cruel, very weird or just a bit eccentric.
From what I know of Welsh (note that I am not fluent at all yet, so it's very possible that I'm wrong), it could be any one of three origins.
The first being ⟨gwen⟩ + ⟨wyn⟩ + ⟨wyn⟩. ⟨gwen⟩ is the feminine form of the Welsh word ⟨gwyn⟩, meaning "white" or "(spiritually) pure"; I find this a bit odd to use in this name, given that Gwenwynwyn was male, and the gender norms of the time were very strict. ⟨wyn⟩ is the soft mutation (Celtic mutation being a grammatical thing) of ⟨gwyn⟩, in this case occurring because the second two elements are descriptive of the first. This would mean that the name Gwenwynwyn means "white (f.) white (m.) white (m.)", or "spiritually pure (f.) spiritually pure (m.) spiritually pure (m.)". This is a bit weird honestly, but it is quite amusing to think about.
The second origin would be from ⟨gwên⟩ + ⟨wyn⟩ + ⟨wyn⟩. ⟨gwên⟩ is the Welsh word for "smile (noun)". This would mean that the name means "white white smile", and possibly that Gwenwynwyn ab Owain was born with teeth. This one actually makes sense to a degree, and it is possible that the double is so as to avoid confusion with the unrelated word ⟨gwenwyn⟩.
The last option is that it came from the roots ⟨gwenwyn⟩ + ⟨wyn⟩. The Welsh word ⟨gwenwyn⟩ means "poison", and is cognate with English "venom" (both come from Latin). This would make the name mean "white poison" or "spiritually pure poison". I have no idea why anyone would name their child that.
Anyway, while I love the name and so do all my friends, I am quite confused by what his parents were thinking lol.

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