I like the more surfboard like boards. And the wait is never a problem for surfboards really but the skimboards its a huge difference.
I have a fiberglass ZAP that is heavy but i like it none the less lol.
I think the best most surfboard like board i have ridden is the APEX carbon fiber board. The rails are nice and round not cut off like most skimboards.
post some pics of this board in use, it looks cool
I would go for some super tapered sharp style rails in the tail. My friend has a Firewire that gets super sharp in the tail, I think that would help sticking to the wave. Thickness and length also depend on how big you are and how far out the waves are breaking. You can't hydro on the maui right?