You are asking some valid questions here and I will answer with my opinion for me.
I currently don't listen to much analog at all and see no reason to change anything with it.
I have used a fair amount of different Dac's over a 5 to 7 yr period and feel like I have upgraded in sound overall with what I use now.
Direct stream
Direct stream Jr
Yggy
The Yggdrasil is the newest and was mainly bought to compare with the Jr and be used in my 2nd system.I use the direct stream in my main system and I haven't tried the Yggy there.Maybe I need to and maybe different cabling as well needs to be tried.
The direct stream with the latest Huron software is the best Dac that I have ever heard or owned,do you have any suggestions.
Best,
Kenny.