Yes complete sense! Most times compression under 100 won't even start! With that said I'd do a leak test on it since you had the top end off, It may not hold compression because the base gasket area leak, reedcage area leak, head gasket leak, maybe the hissing isn't the normal sound?
Any chance of a video?
Well the gasket are all brand new for the top end and came with the Wiseco kit. They are Athena. I mean it is a slight hiss and I haven't done a leak down test yet for two reasons.
One because I don't have a kit or haven't had a chance to go get the stuff to do it. Two because like I was saying with the cylinder and head on the bench turned upside down, spark plug in and tight, and the piston with the rings on and compressed in the cylinder, I can push it down to where it gets past the ports and where it is supposed to start to compress and it will do so but as I push harder and faster it slowly goes down and that is when I hear the hiss that sounds like it is coming past the rings or through the ring gap which seems to me that the leak is nowhere under the ports in the cylinder.
What I mean is that if it is leaking off the compression around the piston as it goes from 1/2 up the cylinder to TDC then the first leak would be that one. So if there were any leaks below the compression range then I would find those after the compression area is sealing. Right? Unless it is normal for it to slowly hiss off that fast or that much which I don't think it is unless you stop putting force on the compression stroke.
I know it wouldn't hold it like an air tank would but I would think that it should hold fairly tight even pressure until you let up off the piston. It does however take a whole lot more force to pull it back up. I will try to get some video of what I am trying to explain as soon as I get a chance and assuming my stupid phone video format will work otherwise I will have to covert it to a usable file format to work on here or youtube.