I remember skating the Jake Johnson Pro Model debut board and that thing was insane. It said it was an 8.5 but it felt wider, it had the most concave out of any board I've ever skated, also, the nose and tail were very steep so I would constantly eat shit because I had to smack the tail down way harder just to ollie. So sometimes alien shapes end up being really crazy, if you like a lot of concave, and a steep nose/tail, then Alien/Habitat boards are the right board for you. Also, I really like the Old Skool's recently released, but one time I got a pair that were lying around my shop for a few years, they were super old. I think the rubber on them expired because they felt really stiff and hurt my feet. I compared them to recent Old Skool's I've skated in and they said they were made in Vietnam as opposed to China. Maybe that's the issue?
Anyways, I'm super picky about my set-ups also and I hate buying all new shit and then not having it work out for me. Best of luck to you sir.