The big thing we tangle on is always digital vs. analog. Oh boy.... Zzzzz... I've cut tape and editing on analog sucks. Noise on analog is not ideal. Compression and 'natural' bottom end warmth are nice. But that's where it stops. Most of (all of?) these things can now be simulated by plugins. We don't even have to say digital has won because it's so obvious. Analog is there for the minority purists.
This debate has between us has taken many hours over many years. Oh yah, let's not forget vinyl too!..
I've had to recently redirect the argument to musicianmanship, which I feel is really where the rubber meets the road. It all starts at the source. If your source sucks, then you'll have some work to do to fix it. Stuff like autotune, sample triggers, etc. In this way, analog is better as it will demand more of the musician's performance. Hard to swap out the kick drum on analog.
All in all, I personally don't think any non-studio experienced audiophiles would know if something was recorded digitally vs. analog. There are so many things you can do now and unless you know those studio 'tricks', you can't even tell. This has already been the case since the 90's I think. Everything can pretty much be simulated, processed, filtered, chopped, moved, etc.
One great resource for all this is Ken Andrews. Look him up. He's got a lot of great stories and insight on recording.
My advice to my friend: learn the tools and use what make sense artistically. But debate for theory's sake is pointless in my mind.