A lot of people have had this same problem in the past. Managing it is a problem but there is a solution. Establish a policy that all regression testing be done within the two latest versions. If it doesn't run now and it did a year ago consider it a different problem. This is the only solution that has worked in the past. It requires a test suite be built that can easily test Windows, not Wine, and it requires that the tests be run before the next version comes out. Versions need to come out at longer intervals with the minor updates in between. This is similar to what is happening now except that when 0.9 goes to 1.0 or 0.91 all previous versions should be discontinued. I suggest setting 0.9 as a base and fixing what is broken in it without any regression testing. Do regression testing as monthly updates come out. In six months or so bring out a 0.91 version and kill 0.9. Trying to regression test back to the original version is likely to have you trying to run 8 bit code.