Update : so my cylinder came back from the shop bored 1mm over with another new piston to match. I'm still only getting about 90 psi and no start. I'm completely baffled now.
carb is good
Valves are good
Piston and cylinder is good

ive tried everything I can think of here. I really hope someone can come up with something else to try.

I'm starting to wonder about the decompression lever. If I have the spring in it when I crank the engine it shoots the lever downward against the head. I also notice when it does this it sounds like there is no compression at all. So I took this spring off and just let it sit level with the bike facing toward. If I pull it up I can feel it click into place and it resets when I hit the starter.

 

Update again.
after messing with the the quad I finally got it to start consistently. However...
it's not idling correctly at the moment. I have been just keeping it going with the throttle long enough to heat the engine for the piston break in procedures. Not sure if that has something to do with my next issue.
I can not get it to move. I can switch through all gear just fine but it gives no power to my wheels. I have noticed when I go into first from neutral is almost wants to kick forward ever so slightly but then nothing. I get nothing through all gears. I thought it could be the shaft not engaging so I took it out again and watched the gear from the case spin. It goes faster as I accelerate and move thru the gears. It Also spins freely in neutral and locks when in gear which leads me to believe its functioning correctly. My rear end is not locked up and can be pushed around easily and I also tested the shaft. When I put the shaft in the knuckle and rotate it by hand it moves the back wheels as intended. Same when I put the shaft in and push the bike it rotates the shaft and the gear from the case just fine.
it seems to me like when I'm shifting into gear from neutral its kicking me back out but the indicator lights dont tell me I'm back in neutral. Maybe some rev limiter or something to do with the auto clutch?

 

What was the issue that fixed to get it starting consistently? Dealing with the same issue it sounds like.

 

Once I had the cylinder bored out and got the piston to match it raised my compression. I'm pretty sure that was the fix to the not wanting to consistently start. I fixed the idle problem as well. The idle turned out to be a bad seal on my choke plunger of all things. I replaced it and now it purrs well.
what bike/ issues are you dealing with. I'll see if i have any insight