Alas, it doesn't give us the same feelings, my friend.
Of all the Ed-names... I like
Edison the best.
Edsel second and
Edward third.
Edwin makes me think of a pudgy boy with freckles and round-rimmed glasses. Not that that is such a bad thing - but... well it's such a specific image.
Edgar gives me specific images too, but they are more quirky, old-man visions... so
Edgar could be arguably hipster.
In any case - the name itself works if only for the nickname Win. And, I won't knock you for liking in, since it is technically a classy name, that is easy to spell and say and has no negative connotations.
As for your nicknames... spot on.
Elias,
Josiah and
Tobiah are great... that "ia" sound fits perfectly. I like
Edwin Tobiah the best... but I might change my mind in a moment to
Josiah. It's a hard pick. Have you considered
Tobias or
Josias?
Samuel as a middle is a bit expected, but creates a strong combo you can't argue with.
Elijah works, but not nearly as well as the others, imo.
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"How wonderful it is that no one need wait a single moment before starting to improve upon the world." -Ann FrankMama to my "bright star"
Clarisse Bituin and Wife to
Julius.
Mahal na mahal from our little family to yours!