Take a look at AzuraCast. It offers a web interface to set up autoDj and other stuff. I think Station Playlist is still the standard for broadcasting. That, or Edcast if you want to do live shows.

tried following a more thorough liquidsoap guide and was successful to almost every step of the way... until it tells me to run liquidsoap itself... I get the error that liquidssoap.service is not found. Googled for it, but nothing useful. I am susprised there are no more options for this.... but again, I guess that trying to do all of this from a mobile data connection is still too a bit ambitious.

I used docker with azura cast, but I still suspect it is my connection. Still, I was finally successful with liquidsoap!
not the most elegant way to do things, but I followed that guide I posted above, and updated the syntax according to the official liquidsoap documentation I found out that the error was due to error in my .liq configuration script because I went to the folder where the .liq script was, using terminal, then typed
liquidsoap blahblah.liq
and got descriptive errors from the program, most of them were syntax errors. Stripping the file though, gave me clues as to what was working and what was not. I still believe liquidsoap really needs to improve their explanations of the stuff, but for me it was enough to make a folder called music in my home/name directory, upload some tracks to it, and then use the script like this:
beging content of file
# Music playlists
music1 = playlist.safe(reload=86400,"~/music")
#I will take care of a default file later and this one has less tahn 10, although very long tracks
#so I'm good forcing it as a safe fallible playlist for now
#the reload before the path refreshes the folder every 10 minutes so if
#I add something, it will be playing eventually.
# Start building the feed with music
radio = random([music1])
#this creates a variable named radio and plays the folder in random order
# Stream it out
output.icecast(%mp3,
host = "localhost", port = 8000,
password = "WhatEverItMightBe", mount = "jam",
name="the most boring radio ever", description="ultra blahblahblah", radio)

end of file content
When I did
liquidsoap blahblah.liq
it all worked. A bunch of messages were displayed with the status of each track and so on.
I went to my.host:8000/jam
using various players and it was playing, using the "the most boring radio ever" as the station name and unknown as the title.
You can tag your media files properly using whatever in windows, then uploading them to your server, so that artist and title are displayed correctly.

oh, I have heard of AltaCast before but wouldn't have thought it was accessible for windows.
Still, I plan to leave liquidsoap for 24/7 transmission and have it interrupt when live streams come in. I will give that one a try as well.

thanks for that.. I am not running any web server, but I still suspect my data connection plays into this as a git issue regarding what happened to me also showed up, blank pages loading for a azuracast, even with different browsers and that was the final coment on it, so I suppose it applies for me too. Still, I need to get more familiar with liquidsoap scripting language, but it works for what I need for now as a nice auto dj type thing

Can I play the files from the folder instead of a playlist? If I can, could anyone give me an example code?

Well, I got an error on line 5, char 3-17. I don't know what the problem is though. I also have a look in liquidsoap quickstart, and my code has written exactly that. Will debug it again tomorrow, now need sometimes to sleep.

Hi there,

My liquidsoap configuration starts below:

Also, you don't need to use WinScp. You can use SFTP (secure transfer protocol) that are preinstalled on Mac, Linux, and recently windows 10.

It says error char 8-17, syntax error!

Yeah, the SFTP thing is pretty useful I don't install any third party software to manage file on my server.

I am happy! finally figured out how to do what I wanted to do, although I know it can be done more gracefully

this will do the following:
1. Get all the files inside a folder named music and play them in random order, reloading them every 24 hours.
2. When you use anything to connect to your icecast using live.mp3 as the mountpoint, the main mountpoint, in this case mine is named jam,  will pause whatever it is playing, and switch to that immediately, abruptly, no transition sound, no warning. You are now live!
3. when you disconnect from your client, it will resume playing, or continue exactly where it left of. Of course, your listeners will never get dropped or anything, and they won't need or have to do anything, either.
start of main.liq file:

# Music playlists
music1 = playlist.safe(reload=86400,"~/music")
radio = random([music1])
#Add support for live streams.
full =
  fallback(track_sensitive=false,
           [input.http("http://localhost:8000/live.mp3"),
            radio])

# Stream it out
output.icecast(%mp3,
host = "localhost", port = 8000,
password = "YourIcecastSourcePassword", mount = "jam",
name="jams radio", description="experimental", full)

end of main.liq

so now, a few remarks:
This is really sad because there should be a different port probably for connection, and also it should be done using the propper harvor input feature so that you can use a different password, protect your radio from anyone  that knows your source icecast username and pass that you have configured there, from just interrupting your stream and whatever... but it gets the job done. For now, its what I need. Hope it helps someone as well.

awesome that is working for you!
as noted, I think the documentation provides great examples and really shows off the impressive features of such a robust great software, but, the lack of a more detailed explanation of the code really is something that sets anyone back. Especially, the syntax of this and that, and why should you enclose things into braces and how you have to put a  variable inside of another (like radio inside full) to achieve the desired outcome... in this case, full is a source that also goes to the same output, shares the output of radio, so that is why they have to be nested. But that is not specified anywhere in docs and not all of us really are that familiar with that kind of programming language.