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
had a dealer tell me there isn’t going to be a major step forward going from my $1500 Nova III to the Modwright 9.0/x. At double/triple the pricepoint from 9.0/x how can this be? Anyone else please feel free to help educate me."

The tube phono presentation will offer another perspective and the ears will tell you stay or go.

Maybe a decent "budget" tube stage can show you what the fuss is all about-https://www.analogplanet.com/content/hagerman-audios-tubey-quiet-trumpet-mc-phono-preamplifier


Mikey and others here say it’s good.

"very small 9 x 13 x 8 ft room"

near field should be like being between giant headphones with those Sopras. 
Just something else to try. YMMV
http://www.cardas.com/room_setup_calculators.php

Pulling the speakers out more, and even closer together along with your seat I imagine would less room interaction? 
@tablejockey 
I'm almost sitting on them. 46" from front wall and 25" from side walls. Bass is slightly boomy, but bass traps eventually. 

So cost isn't always a factor, and maybe not within someone's "taste", but at this level it isn't indictive of more resolution, depth or space? I figured the midfi is where everyone is fighting over to gain market share and sonics are held over lifestyle brands. I'm off the mark I take it?
If you can stretch for it, try LS footers for speakers from critical mass systems.  They decouple your speakers from the room in a wonderful way.  In my system they removed all traces of edginess (yes edginess) and boom.  Their CS footers for electronics and TT's are no slouch either.  A single set of these under your TT may give you a relatively cheap upgrade that would obviate the need for a component upgrade.  I say may, because I don't have a TT, so my experience limited to what they did with electronics.  Check reviews. 
You can't tell what is your weakest link just by playing your system as you can't know what component is doing what.
You have to swap out successive components one a a time and observe the changes.  Experience listening to many other systems will also help.

You also need to decide if you want to be a tweaker.  You can add tweaks, again one at a time, retaining your present system and determine if you think any changes they make are positive or not.
@ j-wall 

Think I would focus on the phono stage. not sure what your budget is but would see if you can stretch and pick up a used Chinook.