Worth pursuing analog sound from digital?

I love vinyl also.My brother has a nice set up that I enjoy from time to time.If I could afford to do both I certainly would,and a reel to reel deck,and,and.....
I think it takes even more time,tweaking,and $$$ to build a really good analog system too.My digital system sounds way better than my analog system ever did just because of the effort I've expended on it.I don't think any one way to enjoy music is superior.The thought and effort put into the fine tuning is what gets us to our individual nirvana.My deep thought for the day:-)

I have an Ayre C5xemp.. and vinyl....they sound different but both are enjoyable

Get an ifi iTube2 and call it a day. 

I sometimes enjoy high quality, high res digital - for about 30 minutes. Then I want it to end.

I listen to analogue for hours. 

I sense that the definition of a digital gear sounding "analog" is going to be different for everyone and for some may be life long pursuit.  For what its worth, last weekend at the Rocky Mountain Audio Festival, I experienced the Innuous USB re-clocker that they will be selling for $3k.  Putting the cost aside, I did experience the A/B testing with it in and out of the system multiple times, I did notice and felt a clear and greater sense of "ease" in the music with the reclocker...Interesting that after the event I looked on their site and the feeling of ease is what they talk about in their marketing. Did it sound more "analog".. I can't say, only can share what it made me feel.   I share this because even with all the great DACs that have been mentioned, I for one am wondering if some form of a USB reclocker (this flavor or other) would bring additional benefit to them, including tube based DACs or even ones that do reclocking internally and do isolation and noise reduction.