Have an old MBP 13 still on Mojave.
Installed and running fine using CrossOver 21.
The installer crash is back so you need to change the bottle to win98 for install. According to winehq this bug is fixed in wine 6.15.
I recommend customising the install to exclude anything ActiveX related and include the source files for CRT.
Install MDAC 2.8 before applying SP6. You need to extract the contents of vs6sp.exe to run the service pack setup.
There are a couple of annoying issues with mouse control after switching windows but I found you can workaround them by using a keyboard shortcut when that happens.
I tested debugging, setting breakpoints and stepping through/over and it seems to be fine.