The most entertaining thread I've read in a while! Lots of great points and specific recommendations have been made. So let's talk about UX.
User experience preferences should be greatly taken into consideration. Much has made of the downsides to vinyl, like cleaning records. I don't mind spending an hour or two cleaning a pile of LPs, slipping them into a nice new sleeve and knowing they'll be clean basically for eternity. Other loath the core, don't do it, and then complain about "clicks & pops" as if they are inevitable. They aren't.
Does ownership of a collection matter to you? ...full size art and liner notes? The whole millennial vinyl craze seems often as much about the physical experience of playing/owning/displaying records as the sound quality.
On the other hand, are you a playlist junkie? If so, digital is clearly your friend, not much debate there...70s mixed tapes notwithstanding, ha.
Flipping albums, especially with audiophile 45s just isn't for everybody. Some love the required focus and get more out of the music, while others would rather play a song, turn on Roon Radio and let it go for hours at a time. Side-note: gotta admit that adding a tonearm lifter is something I'm glad I did, and can be a real stress reducer at times.
On the digital side, how tolerant are you of software bugs, Apple & Windows updates breaking things, and buggy wifi/internet connections? Recently I spun about 5 albums while holding & talking with AT&T internet and Eero tech support teams over issues affecting my audio streaming...irony!
Which tragedy hits home: the friend whose basement flood ruined a rack of album covers or the friend whose hard drives crashed and he lost all his hirez downloads?
Does post-pandemic record shop & garage sale browsing sound like fun or a chore? I am always energized by a couple of hours LP-hunting!
OP, it's worth asking your friend about these considerations to get a sense of their mindset, habits and that may point you to the right side of the fence. Then get down to specific gear.
Personally, I'm put a small amount into a Raspberry Pi, Intel NUC running Roon and a cheap decent dac like SMSL or Schiit and invest the other 80-90% into analog. Agree with comments about digital depreciation. This route would allow a change w/o huge loss down the road if he'd rather go all in on the digital side.
Cheers,
Spencer