Just remember the difference in neck pockets between strats and tele's if you do go that way
How could I forgot that

:) Yeah, in this case I'd round off the heel of the Tele neck, rather than carving up the pocket in the Strat body - the overhanging 22nd fret would hide the mess. And I'd have the option of changing to a conventional Strat neck at a later date.
From Warmoth it's + US$45, as they would get a paddle headstock and cut it by hand in Tele design... all handwork from them is that price...
I'm nearly sold on the Tele idea, it works doesn't it? :)
I would tell you: not everybody will like it, but what is
really important is
you like it... So, if you like it, goe for it! I think it's a little bit odd, but nice!
EDIT: looks better to me that than the Strat headstock on teles!