While I am glad you are using listening techniques to make your decision, your premise is incorrect IMHO. The processing technology alone does not dictate SQ but rather the design intent of the engineering team, especially the combination of the processing technology and output technology. While outside of your price point, I will give you four examples from my personal experience in choosing my DAC. Each has different processing/output technology - the Mola Mola Tambaqui (proprietary/SS), the Bricasti M1 (switchable chip or ladder/SS, the AR DAC9 (chip/tube), and the DCS Bartok (ladder/SS). Each is near world class in its own right. Each has similar SQ attributes while sounding different at the same time (further elaboration is another discussion). The point is ESS chips implemented in quality designs sound great and some ladder processors in inferior designs do not. I had a Wyred ESS design for years that had the clarity you seek, sounding “analogue” like.
+1 @ghdprentice and though I hate to say it 
@audiotroy. At your price point it is difficult to get what I describe and what you seek. I personally recommend you seek a preowned retail $3-5k DAC regardless of the processing technology. Preowned DACs usually sell for 25-40% of retail.
R2R next? Don't like ESS
Can you recommend a good 'starter' R2R dac? I've been through a number of ESS Sabre dacs and they're not for me. IMO, they lack a certain transparency that I'm after. Point of reference: The *only* dac that I've heard that is decent to my ears is a 10yr old Maverick Audio D3 w/ Sparkos OpAmp swap. *This* was great. Alas, I sold it because I thought I could do better with something newer.
Geshelli's offerings have piqued my interest - the J3 in particular - but it's an ESS chip. Wondering if I should make the jump to something R2R - Denafrips, Broder Patrol.. thoughts?