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I think the Airport Express does music streaming over AirPlay, so he probably needs something like the now-defunct Chromecast Audio, or, as you say, a Raspberry Pi with a DAC/Amp.
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Currently I think most folks doing this are using RoPieee to get Roon onto their Raspberry Pi, here’s a link on doing that, RoPieee Beginner’s Guide .
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So, for instance, this HiFiBerry DAC+ bundle give you audio out which you can run into your speaker.
Lots of good input here already, so I’m mostly going to just piggyback off the points others (see quotes above) have already made and provide a bit of my own input/perspective/experience:
- The way I currently do it is primarily Google Chromecast Audio’s. I currently have six of them plugged in and two of them on a shelf ready-to-go. They were super-cheap, which was the whole appeal, to be able to outfit your entire home with some at-the-very-least “entry level hi-fi” whole home audio quality for just a couple hundred bucks total, was super cool and really got me going at an earlier age when money was tighter.
Roon’s Advanced Audio Transport does, IMO, provide superior sound quality. My RAAT-capable endpoints do tend to image better and sound more open than when the exact same speaker+DAC+Amp signal chain is instead fed the exact same FLAC files losslessly via Google’s Cast protocol.
Sadly, for the cost-conscious, as others have already pointed out, Google killed the CCA.
- RoPieee is pretty easy and slick. I was admittedly a little nervous myself, as I am very comfortable in windows and android but only had limited (professional) experience working in a Linux environment. But you don’t need much (or any) linux skill at all; all of the hard work has been done for you by the creator(s) of the project.
The one I bought from Cana-Kit, with USB output, was VERY simple to assemble. I personally had a pretty poor experience trying to assemble my HiFiBerry one with the Digi+Pro hat… I needed the SPDIF output for that zone, so I tried this instead of repeating the Cana-Kit one that had worked well for me. I’m not very handy, so maybe others breeze through it. But I can’t very easily recommend that specific Pi plus Hat combo based on the experience I had…
RoPieeee works over RAAT, which means they can be grouped together with other RAAT-supporting devices (like my Oppo). I think I need to try to configure a static IP for it, though, because I am having minor/temporary network unreliability when the Pi is grouped with my Oppo, and I wonder if that would help it…
- Unfortunately, there aren’t a lot of other cost-effective alternative solutions post-CCA other than a Pi. The Bluesound’s are maybe the most affordable one I’m aware of, and if you have a larger-ish whole-home configuration, at $550 a pop, I personally don’t really call that “affordable”. You can buy yourself a pretty nice new pair of speakers for the same amount of money it’ll cost you to replace four Airport’s with four Bluesound’s…