I like to listen to web radios of all kind and like to discover new ones. But if you want to keep me from listening to your station on a long term try to avoid the following:

1. Bad stream quality
   FM was invented in 1925 by Abraham Esau and we can listen to good sound quality radio for over 75 years. Why should I listen to your 64 kbps or even 24 kbps radio? If you can’t afford the bandwidth then try at least to spice up the stream with AAC.
2. Ever changing IP address
   If I like your radio i will put it in my bookmarks. It’s quite anoying if I try to listen to your stream the next day and the player can not find it. More often than not I’m too lazy to look for the new address and simply delete the bookmark. Get a domain name, it’s cheap.
3. No ID3 tags
   I like to know to what song I am listening right now and my media player will tell it to me if… if you put the ID3 tags into your stream.
4. Repeating always the same songs
   Classic Rock, New Wave or 80’s collections should contain more than your 20 favourite songs. Such small collections will keep me one hour with your stream and off you go.
5. Force me to install any plugins
   If you want me to install any plugins because you’re using some esoteric codec you’ve lost a new potential listener this very minute.
6. Not following any conventions
   There are some unwritten conventions which will make the life of your listeners easier. You should for example put the station’s name and any other additional information in round brackets behind the ID3 informationen. This will enable the lyrics plugin my to distinguish between them and to display the correct lyrics.
7. No MP3/OGG stream
   Some people want me to use their almost unusable Flash players to listen to their stream. Despite the poor sound quality most of these players offer I don’t want to have an open browser tab or an extra browser window on my screen. I like my media player and it’s the only application use for music (OK, the last.fm player is an exception).

Most web radios are aware of the bad habits above and try to avoid them and if not, many will change their streaming after a small hint.