How easily can you distinguish between different DACs?

The SQ and differences in character of DACs can be profound. The rest of the system seems to determine how much of that you'll likely hear. 

One big difference for me is that ESS based DAC's seem to always be too bright sounding on my system and headphones. Both have ribbon drivers. I ended up with an R2R DAC that sounds much better to me. 

I think the best way to decide how you like any new component is to live with it for a while.  If you don't like it, it will become obvious quickly.  If it's close, you can go back and forth and compare.  Play lots of different music- see if you enjoy things you hadn't with the prior component.  This seems to be the way reviewers do it.

I don't have really expensive DAC's, but what I do have are:

Bryston BDA2 Dedicated DAC

Internal DAC on my McIntosh C47 preamp

Internal DAC on my HEGEL H160 integrated

Topping D30 Pro Dedicated DAC

Internal DAC on my Bluesound player

When I have swapped my DAC's around, I really can't hear differences...The big differences for me are with speakers. Even the non-golden-ear listener that I am can hear big differences from transducers! I can only guess if I did a perfectly setup double-blind experiment with DAC's, I might be able to hear differences, but they would be ever so slight.

If you want cheap crap that will eventually fail then buy cheap crap. As some here with old ears say or no listening skills say. My post for the day.