Spend my money

I am not sure that I would dismiss a subwoofer.  The OP says he has to much bass, but it could be that he has rear ported speakers that are to close to walls.  If he uses a front firing sub to handle low frequencies it might eliminate the boom effect and relieving his mains from bass duties can enhance the midrange.

Funkbass4, I think you should get a cookie jar and continue saving. You love music and you want to do it justice. Save for a system that you will be happy keeping for a while. Do not waste money on intermediate steps unless there is a specific problem you are having that you want to address now. 

What’s your room like? Have you looked at acoustic treatments? Is your chair comfy enough? Do you need a rack to better organize things? Do you need to reposition your layout? How about a headphone stand? Do you have a decent surge protector so your system doesn’t get fried by lightning?

What are you using the Sys for? Have you considered adding a Loki to your stack of Schiit to help control your bass? Are you even using the tuner or DAC in your TA-100? Could you consolidate a bunch of functions with a better integrated and ditch a whole bunch of cables? There must be something out there at a reasonable price that has a good DAC, phono stage, and headphone output.

What do you think you’re missing or do you just want to do “better” in an undefined, unplanned, organic way - the audiophile equivalent to swimming upstream to spawn?

Finding such a majority I feel could at least given me some feedback about what components might be worth upgrading first.

Won’t get that here. What you will get is a hodge podge of recommendations.You’d do as good to plaster a wall with a random assortment of Stereophile and start throwing darts. But don’t take my word for it, scroll up and read. What I said. ;)

The truth is everything matters. So take one thing at random- speaker placement. You could spend the rest of the day moving and measuring and listening and get that one thing dialed in just perfect because I can guarantee you right now its not, and just that one thing would be as good an improvement as any component your $500 will buy you. Or you could put that same $500 into finding a really good power cord. And everyone will howl but the truth is you will hear it and it will massively elevate your system. Or you could put a grand into a really good cartridge and be amazed that way too.

Its precisely because everything matters that no one can tell you what you want to know. Asking a bunch of random dudes is fine over a beer and there’s definitely a crowd here acts like that’s what this is, a bar, where you go to shoot the breeze. To answer your questions seriously we need to know quite a lot about you. Not your component list. You. What you like in the way of sound. What you want in the way of a system. Not just now but years from now.

There are for example two major schools of system building- One and Done, and Lifetime Achievement. One and Done you buy a bunch of stuff all nicely matched around the same level and that’s it you’re done for years maybe forever. Lifetime Achievement you aim to upgrade not just components but the whole system over the course of many years.

If you’re Lifetime Achievement then there are times when you will stretch to buy something like a turntable that is quite a bit better than people will tell you your system deserves. But it will last you a good long time and during that time you will gradually upgrade everything until maybe one day its the turntable that needs upgrading. Or amp. Whatever. Point is not what, but how.

Right now you are focused on what to buy. When you should be focused on what are you doing? Because once you know that a lot of these other things will fall into place.