First of all I've been a Winamp user since the early days and been through pretty much all versions of it and I'm extremely happy that it is still alive. I haven't been an active community member but I'd like to offer some of my opinions and observations about this thread and others before it.
FEATURES AND EASE OF USE
It is my opinion that for now Winamp does not need new major features since it already has pretty much an unmatched feature set. This has it's advantages but it also has some major disadvantages. As was mentioned on by another poster the common man likes to have a lot of features as long as they are pretty much invisible and everything works out of the box.
The settings and UI
should be revisited, reorganized and the more advanced settings and features set aside for those of us who want to adjust and use them and know what they are intended for. There should/could also be more explanatory information along with the settings as the common man do not like to browse through long help documents and find information instead of using the product.
Many unknown options cause confusion.
This is a fact that applies to the common people. Even the simplest things like understanding that a Gmail account is actually a Google Account that is used across all Google services: Android devices and their software downloads/purchases, Checkout for payment processing, Google+ and so on. Even remembering account passwords tend to be too much for many and I actually remember several of other peoples passwords because they call ME when they have forgotten their passwords. Just last week I opened up a locked phone because the owner did not remember the password she had set up for her Google Account just a few weeks before. I've set up so many systems, devices and phones over the years that I know it to be a cold hard fact that the common man are "stupid" when it comes to technology. This applies even to my own generation which has grown up around computers and mobile devices.
would be the only major part of the software that I'd like to see improved (or it should be removed completely and forgotten). Currently the video support is a bit hidden, management features are almost non existent and it feels like it's been thrown in there just as an experimental feature. Where are automatic libraries for TV shows and movies for example? Video format support should also be extended and it would be nice to see something like FFmpeg integrated for codec free playback although it is most likely unrealistic to expect this at least in the near future. There could also be some licensing issues too. This would make even blu-ray playback possible and we wouldn't need KMPlayer, VLC or K-Lite Mega Codec Pack.
Other existing features
should of course also be improved. This should be obvious. Nothing is ever perfect and there is always room for improvement and innovation.
And for other advanced stuff like ASIO support I'd like to say that people should be realistic and think about what can be done and what is possible with the available resources. There is a reason why it is quite rare to see support for it. The FFmpeg integration I mentioned previously goes into the same category. I doubt that Radionomy will dedicate all of it's resources on the future development of Winamp and hire a large team to work on it full time. But who knows, it would be great if they did.
STREAMING SERVICES AND MARKETING
If we start to think that Winamp and SHOUTcast should be set up against other streaming services (like Spotify for example) there shouldn't be several products like Winamp the media player, Winamp Cloud (if it ever will be) and SHOUTcast. They should be combined under a single brand like Winamp Music. Again I point out that many options create confusion. Also as was said before SHOUTcast is currently very different from services like Spotify and it's very purpose is different.
There should also be more visibility in (international) media especially trough channels that the common man uses. I'm from Finland so I don't really know how visible Winamp and SHOUTcast are in the US (for example) but here they are pretty much unknown for everyone who isn't tech savvy.
The would be competition
Almost everyone who listens to digital music here in Finland at least knows of Spotify (I've never paid for a subscription but have bought a lot of individual tracks when it was still possible). It's the only service that has I've seen really marketed for the general public (through FM radio advertising for example).
Google Play Music (I'm a subscriber) and Xbox Music (I was a subscriber) are both also already available here but for now they aren't widely known and unfortunately it is going to stay this way as long as they are being mainly marketed only through Andoid, Xbox and Windows (Phone).
iTunes of course has the advantage of being the pioneer in digital media distribution but even it is not that well known here and it is falling behind because it doesn't offer similar subscription options and is available only on iPhone and iPad (on the mobile side). If Apple want's to stay in the competition they need to wake up and start to offer their services on other platforms as well or they will end up like Nokia did with mobile phones. Microsoft has already done this with Xbox Music and also with Office Mobile and other products.
This would be important for the software and services to gain global market share. All of the previously mentioned "would be competitors" are available in finnish. I like to use english when ever I can mainly because technical stuff often doesn't translate that well into finnish but the common man should be able to use it in their native language.
The current translation system should be much simpler if it remains community driven. I've translated some programs into finnish and have though about translating Winamp too for a long time but I simply do not have the time to learn the current translation system. There are also some services like Transifex (XBMC for example uses it) to make community driven translation easier. Not an easy task I'm sure and would most likely require a lot of changes to the base product.
there would be the need to provide support and service on a much larger scale if Winamp and/or SHOUTcast would be made into something more than products for the community like they pretty much are today.
First and foremost Winamp should be made into a newer, more streamlined, more simplified and even more modern version that can rise back to being the number one media player it once was, so very many years ago.
I thank you for reading if you ever got this far