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You asked us about the name "Owain ap Llewellyn" in the context of late 14th century Wales. First, we would like to applaud your own initial reseach, which has led you to choose a name that is very authentic and typical for your desired time and place. The following discussion is primarily meant to suggest some modifications in spelling and to make you aware of the range of possibilities in use at this time.
The primary source we have used here is a list of personal names from Anglesey dated to 1406 (which seems close enough to your late-14th c. target to be the most useful). There were, it is likely, regional variations in name popularity and in spelling, so this information can't be considered prescriptive for the entirety of Wales.
In this document, Owain is relatively rare, appearing twice, both times in the spelling "Owen". However, a 14th century poetry collection known as the Hendregadredd manuscript variously uses the spellings "Ewein", "Owein", and "Ywein", of which "Owein" appears most commonly. The spelling that you propose -- "Owain" -- is the standard modern spelling, and we can find spellings with "-ai-" in the 14th century in (of all places!) French employment records for Welsh mercenaries. These records include the spelling "Owain", as well as a number that clearly follow French spelling rules rather than Welsh ones. In general, in Welsh spelling, the "-ei-" spelling was just beginning to be replaced by the "-ai-" spelling in the 14th century -- a change that was more characteristic of the 15th-16th century. Both are "correct" for the 14th century, but the "Owein"-type spelling would appear to be more "typical" at this point. In summary, the most typical spellings appear to be:
In the above-mentioned list of names from 1406, the name Llywelyn is relatively popular (comprising 2% of the total). In this document, it primarily appears in an abbreviated form, but is also found spelled out in full. The forms we find there, in order of popularity, are:
The spelling you proposed ("Llewellyn") was used in period, however the only examples I can find are from the 16th century, and furthermore, this spelling would be used in an English-language context rather than a Welsh-language context. (In Welsh, the spellings "l" and "ll" represent significantly different sounds and "ll" would not represent the Welsh pronunciation of the second sound.) Although "Llewelyn" appears to be the commonest Welsh-language spelling in your period, the previously-mentioned _Hendregadredd_Manuscript_ also has the spelling "Llywelyn", which is the standard modern spelling as well.
The patronymic marker ("ap") is correct as you have shown it.
Any combination of the above-mentioned spellings would create a very authentic name for late 14th century Wales.
Bibliography
Jones, Heather Rose. "Names and Naming Practices of the Anglesey Submissions of 1406" based on: Roberts, Glyn. "The Anglesey Submissions of 1406" in "The Bulletin of the Board of Celtic Studies" vol.XV.
Jones, Heather Rose. "Welsh Names in France in the Late 14th Century" based on: Siddons, Michael. "Welshmen in the Service of France" in "The Bulletin of the Board of Celtic Studies" vol. XXXVI.
Morris-Jones, John & T.H. Parry-Williams, editors. "Llawysgrif Hendregadredd." Cardiff: University of Wales Press, 1971.
This letter was researched by Tangwystyl verch Morgant Glasvryn.