How do you know what your weakest link is?


I'm  contemplating what to upgrade and need some advice on what my weakest link is? I'm considering either upgrading my Clearaudio Concept Wood to a Performance DC Wood/Ovation with a Hana ML or upgrading my Musical Surroundings Nova III to a Modwright 9.0. Is my table the weak link or is my phono? What will my best gain come from and what should I expect that gain to manifest as? 
128x128j-wall
"I'm almost sitting on them. 46" from front wall and 25" from side walls. Bass is slightly boomy, but bass traps eventually."

Yeah, you have a lot of speaker in that small room. 

"I've considered the Chinook, but I've seen many reports of noise, picking up fm signals and more selling them than keeping them."
The times I demoed one in my system, very quiet.

This looks interesting-
https://www.analogplanet.com/content/hagerman-audios-tubey-quiet-trumpet-mc-phono-preamplifier
@tablejockey I'd be interested in doing a pool for gear. We should get some people together so we can all experiment and try gear. Let's start with the Hagerman. 
"...@russ69 I should probably set up my virtual system on here...."

I thought I looked. Did you post that yesterday? Anyway that was very helpful. I like your system. I don't have much to input other than a cartridge change always brings about a new and different sound. My other thought is I have not heard the PrimaLuna pre-amp but it could be holding you back. You might want to try something else in that position and see. 
@russ69  I actually updated my profile after I thought about it. I'm still thinking the bigge changes will probably come from my table or phono so I'll be starting there before the PL.