I'm reminded of FamiTracker, one of these traditional Win32 (MFC eew) apps which has managed to survive into the modern day with a technological stack largely unchanged, outside of newer compilers and me replacing DirectSound with WASAPI in Dn-FT. But even in simple apps there's a surprising amount of complexity, ranging from threading deadlocks from poor architecture, to a Wine bug causing the window to fail to redraw when resized (https://bugs.winehq.org/show_bug.cgi?id=52903, related https://bugs.winehq.org/show_bug.cgi?id=52515).