Big upgrade with stand alone transport???

I know this sounds like a broken record.You really should try a NON OS DAC.A NON OS DAC has a roll off at 22Khz of 3 dB.This isn't a bad thing either.All that unnecessary hash that's not needed is filtered out.It makes it much easier to concentrate more on the music. I hear no roll off as we humans don't generally hear above 17 or 18 khz.What I hear is a denser midrange as images seem to have more solidity. Here check out this review of the Scott Nixon Tubed Dac/3AX power supply..Dont skimp on the power supply either! Your looking for tonal balance..I'll take tonal balance over stratospheric frequency range any day..There was a time when I chased the super extention..all I got was fatigue and hash.

I have listened to your setup some years back, by coincidence, and if you can get a modest cost/great performance digital cable like Auricle Audio Design Encore Signature IC on the occasional auction on Audiogon you can extract more performance from your gear.
I have been favorably impressed that the Monarchy DIP is beneficial, but have always run what have been considered more expensive digital IC's in a higher end system compared to what you listed for yourself. Then, unexpectedly, the Auricle product did the best for the least cost, a special "find" among the myriad of digital IC offerings on Audiogon.
As far as whether you will hear a transport upgrade, if you can pick up a used JVC XL-Z1050 CDP on Audiogon then you will have a versatile upgrade, either played as one box solution, or used as transport.
There is in your future a better DAC when you read about the new wave of realistically priced (within your budget :>) outboard DAC's such as the Scott Nixon DAC's on Scott-Nixon.com
In conclusion, as Bigkidz posted, consider starting with better digital IC that will play well with any level of equipment.

Thanks alot guys and happy holidays!