My original answer, although it worked with Xcode 8, for some strange reason which is not worth explaining, no longer works with Xcode 9 on a particular client's old project. So I've been using an alternative workflow which is really not too bad.
To work on this project, I open it in both the older Xcode, which can build it with the required SDK, and in a recent Xcode. I put the old Xcode window in the background and do my work in the recent Xcode. When I am ready to test changes, I do a File > Save All (⌥⌘S), then switch to the old Xcode and Build (⌘B). When the build is done, I switch back to the recent Xcode and Product > Perform Action > Run without Building (⌃⌘R). Because the dSYM file format has not changed, breakpoints work as expected.
The advantages are that no hacking of Xcode is required, and the only thing I need to remember about the old Xcode (Xcode 3 in my case) is, mercifully: ⌘B.
One little warning: In this particular project's Target, in Build Settings, it has a custom Build Products Path. This is typical of the way Mac apps were built years ago. To ensure that both of your Xcodes are working with the same product, if your old and recent Xcodes straddle the version which changed the default Build Products Path, you may need to set Build Products Path.
The workflow could probably be made even easier by scripting the xcodebuild
and xcode-select
command line tools, but this is good enough. With Apple's announcement at this year's WWDC about support for 32-bit Mac apps going away during the next two years, my client has some tough decisions ahead in any case.