I don't have subsonic installed on my windows VM but if memory services correctly you can do the following to control services in windows
1. Bring up the services control panel by running 'services.msc'. Just hold [WINDOW_KEY] + r and a run window will appear. Type the command in there and press enter.
2. Find the subsonic service in the list and right click it and click properties.
3. Set the start up type to automatic or maybe automatic (delayed). I'm not really sure which is best.
As for getting a playlist to play automatically. I think I know a way but I haven't tested it.
Subsonic has the rest API which allows you to send commands to the server ( see
http://www.subsonic.org/pages/api.jsp )
You tell the server to start playing the jukebox (user must be authorized to do this). By visiting the site (look at the page's source code to see what is happening) (or using a tool like wget)
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http://localhost:4040/rest/jukeBoxControl.view?u=username&p=password&v=1.2.0&c=dummy&action=start
where username is the username, password is the password for the user that's authorized to use the jukebox player, localhost is the address of the subsonic server and 4040 is the port the server is running on.
adding tracks to the jukebox playlist isn't made very easy though. You seem to need to add the id of every single track rather than using the id of a playlist
You find the track ids of a playlist by doing
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http://localhost:4040/rest/getPlaylists.view?u=username&p=password&v=1.2.0&c=dummy
.
which will give you a list of playlists.
Find the id of the playlist you want then you can get the track ids by doing.
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http://localhost:4040/rest/getPlaylist.view? u=username&p=password&v=1.2.0&c=dummy&id=playlist_id
You can then add tracks to the jukebox playlist by doing
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http://localhost:4040/rest/jukeBoxControl.view? u=username&p=password&v=1.2.0&c=dummy&action=add&id=track_id
If you want to automate this wget for windows is a much better bet.
I think I may look into this more because I've had a few problems using the rest API.
I hope this helps.