Thanks for the idea guys.
I think I may actually go with the Five Wits wig and if I have problems with the widow's peak when it gets here I'll take it off and replace it, because the rest of the wig looks like it would work great for him regardless.
Plus it's cheaper than my lace wig options I've seen on ardawigs.
Rose Lalonde - Homestuck - [god tier] - 80%
Dave Strider - Homestuck - [red plush] - 0% & [doomed felt] - 0%
Davesprite - Homestuck - 0%
Gil Marverde - Ava's Demon - 80%