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Greetings from the Academy of St. Gabriel!
Here is the information we have found about your proposed name.
You asked whether <Kilsayth of Sky> or <Kilwitch> are correct pre-16th century names.
<Kilsayth> is a Scottish place-name [1]. This particular spelling is recorded in 1665; earlier spellings include <Kelvesyth> (1210) and <Kelnasydhe> (probably an error for <Keluasydhe>) (1217). Using <Kilsayth> as a given name would be similar to calling yourself <Harrisburg Smith> or <San Francisco of Boston> in modern times: Place names were not used as given names. However, you could probably use it, in one of its earlier forms, as part of a locative byname [i.e., "(given name) of Kelvesyth"].
You should be aware that "(given name) of X" would not be a Gaelic name. Gaelic people did not use locative bynames. However, "(given name) of X" was used in English, Scots and Scoto-Norman naming. The difference reflects a growing cultural division in Scotland between the Scots-speaking Lowlands and the Gaelic-speaking Highlands. (Scots was a language closely related to contemporary English.)
<Kilwitch> looks like it may derive from <Culhwch>, the name of a character in a Welsh myth involving King Arthur; it is pronounced \KIL-hookh\, which is not similar to the sound you're trying to achieve. This name is unique and its elements are not used in other Welsh names; although it is used in legends, it wasn't used by any historical people. Since it's not a historical name, we strongly recommend that you use a different name.
If you are partial to names beginning with <Cil-> or <Cel->, here are some of the more popular Irish names that fit that model, with their pronunciations [2]. The slash in the names represents a sharp accent on the preceding vowel. The \kh\ in the pronunciations is the hard, rasping "ch" sound in the German "Bach".
These names are all Irish Gaelic names. If you decide to use any of them, then the rest of your name could consist of a patronymic (e.g. <macCormaic>) or a descriptive nickname (e.g., <Ruad> 'red', <Dub> 'black').
On the other hand, if you are specifically interested in a Scottish name, we suggest you read the article "Scottish Names 101" on our website at:
We hope that this letter has been helpful. If we can be of further service, please do not hesitate to contact us.
Arval d'Espas Nord, Alan Fairfax, Talan Gwynek, Effric neyn Kenyeoch vc Ralte and Tangwystyl verch Morgant Glasvryn contributed to this letter.
In Service,
Giulietta da Venezia
Academy of St. Gabriel
References
[1] Watson, William J., _The History of the Celtic Place-Names of Scotland_ (London: William Blackwood & Sons Ltd., 1926).
[2] O'Brien, M.A., ed., _Corpus Genealogiarum Hiberniae_, Vol. 1. (Dublin: Dublin Institute for Advanced Studies, 1976).