As you might know, I keep my station running by using winamp on shuffle with a DSP tool called StereoTool for audio enhancing and normalising.
Our music consists of a very big variety. 1% 50s, 15% 60s, 25% 70s, 15% 80s, 35% 90s, 10% 2000-today (indie stuff)
In a typical hour on WHAR, you'll hear Florence + The Machine, Hall & Oates, Electric Wizard, The Vintage Caravan, The Doors, Green Day, Nirvana, Marvin Gaye, Funkadelic, 311, Weezer and even Toots & The Maytalls
We pride ourselve in being a genreless station and play as much variety as we can.
I have always been a fan of vastly wide range of music genre.. even wider than you describe. It doesn't put me off in the least if a Nirvana song is imeadiatly followed by a Benny Goodman tune!
For the last several months I've been using Media Monkey on shuffle for automation, but that's only because my options are currently limited to what my Surface RT tablet will allow.. But when I get back to using a regular pc I'll bet so happy to be able to resume using something more capable of radio automation - my preferance being Zara.. I really miss some of the little things like having it set up to automate newscast, time, tempature, station ids, psa's, etc..
ZaraRadio is not particuarly any more difficult to use than a plain ole Winamp playlist is, and it's also free, and the little 'extras' it provides really does a lot to overall enhance the broadcast by making it sound better structured even though it doesn't really involve any extra effort.
My point is that Zara is super easy to use, and it seems like your limiting yourself by just using a Winamp playlist. However, you would have to utlize some virtual cables to make use of StereoTool plugin, but it's not that difficult and a one time setup.y
Just something to consider.
.. It's not uncommon for me to bring a laptop up to the public pavilion on the days when I work up there, usually weekends, and unplug the speakers from the XM radio and plug it into my laptop and start Zara up playing a very wide variety of music genres.. I've been doing it for about ten years up there, and it's not uncommon to hear compliments even though most people seem to think it's actually a radio playing, as it also contains psa's, End80radio id's and other short format bits scattered within..
Last year we had a new bartender.. I hadn't brought the laptop up there in a few weeks, so only the XM had played since she had been there. One morning I finally hooked the laptop in an loaded up Zara, it played all day.. At about 3 or 4 in the afternoon the bartender said "I really like this station, it's so much better than what you usually have playing. Bobby tells her "That's not the radio, that's Rich's laptop, he brings that up here sometimes.". She then hollars at me from across the peir "Rich! Get your ass over here!".. She wanted to buy me a drink! (as if I didn't get them free up there if I wanted one anyway). But there's been several inscidents like that over the years in realation to wide genre programming, it always seems to go over well. I think part of it is the anticipation of what might playing next.. it's just not the same ole same ole. It makes it unique.
Incidently, I just tried tuning in your stream but its currently offline.. I recall occassionly tuning into Tiny Harbor Radio sometimes, who also seemed to play wide variety of genres.
I'll second the Zara bandwagon, sounds like a fun format atrain!