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I don't know what's going on since you are using wine, but you can try pressing F12 when the sound disappears to restart the sound interface, that should be identical to restarting the program.
Yeah; X11 WINE isn't exactly the best way to run FamiTracker on a Mac (as a matter of fact, many of Mac OS X's X11 programs aren't well-suited for running on Macs because they're mostly ports of Linux X-Windows programs from the Open Darwin project; many of the ports had flaws that were never rectified before the project went under).
If you're using an Intel Mac, you could try using WineBottler (it's open-source & it's been programmed specifically for Mac OS X instead of X11).
I actually use VirtualBox in Ubuntu, running Windows XP Pro SP3. But VirtualBox is aslo available for Mac OS X & can run other OSes (including Windows, for the sake of solving your problem).
The point is that, if you want to run FamiTracker, you need to emulate a Windows system. The best way to get native or near-native emulation of Windows systems on Macs would be:
1. Use Boot Camp & switch between Windows & Mac OS X.
2. Use VirtualBox, Parallels or VMware to emulate a PC inside of your computer (that way, you can run Windows at the same time as you run Mac OS X).
3. Struggle with WINE on your system (I use the term struggle because lots of Mac users have trouble using WINE & its equivalents; I assume it's Apples way of trying to force people into using Boot Camp).
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Technology: the one thing that's hated & cursed at by all engineers, technologists, scientists & technicians!
I've used Boot Camp, Virtual Box with Ubuntu Jaunty, and Wine.
Not to run Famitracker, but for other things in the past. Virtual Box makes my laptop go apeshit with the fan buzzing non-stop. It eats up too much CPU and RAM power. Parallels and Virtual Machine do the same thing, and also require a partition. Boot camp also requires a partition.
I don't want to partition my laptop. I only have 120 Gigs total with my laptop. When I have to install Windows XP or 7 it'll suck up around 15 gigs in Virtual Machine, Parallels, or Boot Camp. 15 gigs to run FamiTracker isn't reasonable for me, unless if I want to run other programs.
But I don't.
Maybe I can learn how to install Windows 7 on an External Hard-drive. XP doesn't support that feature. I can look it up for Windows 7.
I'm not struggling with Wine. The headphone thing isn't that big of a deal, because restarting FamiTracker takes less than half a minute for me. I hardly ever need to switch throughout the day, so it's more of an inconvenience than a hindrance.
I like to learn how to program within the X11 Terminal and Mac Terminal. I learned how to disable the Widgets in order to free up the F12 button, so that was cool. I even learned how to remap the "Delete" and "Insert" keys which were totally omitted from my keyboard to use it in Wine for FamiTracker.
But, F12 didn't work with the sound issue, haha. It's weird, I don't even know if it's a hardware problem or a software problem.
Actually, instead of using VirtualBox with a Windows XP image on your system's current hard drive, you can load the XP image on an external drive (like a USB key or a USB hard drive).
Apparently, when you use an external drive to load an image into a PC emulator, it will actually reduce the amount of CPU usage the emulator takes up. I remember reading that on VMware's documentation.
But anyways, I'm glad you're finding other (better) methods. However, just as you can install Windows 7 on external disks, you can do so with XP (BartPE is the tool to do this, except there isn't a single plug-in for any sound card, as far as I know).
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Technology: the one thing that's hated & cursed at by all engineers, technologists, scientists & technicians!
Ok so it didn't work. I guess there is something in wine that needs to be restarted. Is it USB headphones? Have you tried changing the audio output device in settings window?
Have you tried extrenal speakers? Plugging in headphones with external speakers doesn't effect the computer, external speakers have volume control on them, and can go louder, meaning you can turn down the operating system volume to consume less CPU and RAM. And, it's less expensive than having headphone sensor deactivated, therefore not letting your computer know that you plugged in headphones/external speakers. The thing is, though, you can't bring external speakers everywhere. But, still, it's better than starting to not like using FamiTracker.