First stop is the http://appdb.winehq.org Look up application remember to click through on version and see if there are any special instructions. Some cases it can be a simple regression in wine code. Flash you normally don't install in wine instead use native Linux version. ~/.wine/drive_c/ is the virtual C driver location. Wine is not windows. If you just copy windows in you end up with more strange problems than you can dream. Run wine from console and on stderr output wine will display debuging information that is sometimes really helpful to know how program failed. I hope my english is read able enough. I am native english with dyslexia your english is not too bad.
