Woodbridge Street and Wilkinson and Shadyglade avenues were all introduced on the same 1923 tract. A bank was listed as its owner, which means the actual mortgagees and developers remain unknown and thus it’s impossible to find any personal reasons behind the first two streets’ names. (Obviously Shadyglade was employed just because it sounds nice.) It may be that the developers left it up to civil engineers with the City to anoint these three streets, in which case said engineers would have just combed through their “idea files” and picked whatever names were available. For what it’s worth, Woodbridge Street was originally called Woodbridge Lane; it was changed in 1933.
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