Self host all the way
I just found it's really overkill for me, as my server consumes just 35mb running icecast, I always wanted something like 0x0.st & ix.io I know linx-server but I haven't found similar on BSD ports.
I got httpd running, it's most simple setup ever.. Just copy over /etc/examples/httpd.conf and retain just two lines (port and root). The chroot makes more sense isolating each web environment, also OBSD directory hierarcy is intiuative. (might look into more)
The most annoying problem I face with my sloth internet is when using IRC, lost track of how many #fix_your_connection channel I'm in. I found out ZNC, I believe this should fix and guess what, it's in ports.
Quick search for "youtube-dl icecast" yeildss an interesting question in stackoverflow, that's similar to some music bots I used in past on proprietary shit serverices.
I use ezstream as source client to stream my opus songs also, xmms2 if I want to add media on fly but it was too old that opus didn't exist when it was created. I should find a source client that support youtuble-dl and intergrate on server (mpd + mpv I guess).