Although I agree that if it’s a small business, it’s better to outsource it to an established business but if you’re serious about doing it yourself, check out OpenDesk/OpenCode. Also, why use your own hardware? A VPS is much more reliable.

Also, add 2FA

Biggest hurdle would be timing, if you want it sound right… Every speaker should be in sync as much as possible

Logitech media server (squeezebox) with the don’t stop the music plugin. It can use different services for context aware playlists and I found last.fm to be a lot better than Spotify. MusicIP used to be a thing on LMS as well, and probably can still be used, that’s completely local but analyzing new tracks is slow since MusicIP servers are down (MusicIP got bought by Spotify ages ago).

2nd, but with just a bash script. Also, I’m forwarding http & https to different IPs and the best thing about cloudflare is that you can restrict those ports to only be open when coming from cloudflare’s proxy. I like the extra layer of security, and dislike that they can see all traffic…