Not to cause more frustration to the mix, but maybe try AVLinux. Use the live DVD so you don't lose what you have. Wine and wineasio are already installed. Its 32bit but its just to see if it works proper. Once you have it running, just run the wineasio in the menu to register it and install Reaper. If it doesn't work, it may something in your hardware thats not working with wine. If it does work, then some configuration issue in Ubuntu.
You may even install wine from kxstudio rather than build it. May be something left out.
Just my 2cents
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