BG, if you want to go with your original plan, you could.
You would need to make the top level and glue on a new strip across the top.
I think you are doing a veneer headstock, so that would cover the top and of you use the same timber I think it would work from behind.
I have seen them repaired and changed like this before and it seems to work fine.
Titebond would be more than up the the task. See my Epi headstock repair - glue only, still holds, guitar played near daily.

Which ever way you decide to go, all the best - you will make it look good either way