TLDR: Every time JSGME tell ask you a yes/no question when you enable a mod, you are most probably breaking something.
Long version:
Every time JSGME tell ask you a yes/no question when you enable a mod, you are most probably breaking something. So don't do it if you are not 100% sure you can , like you have Wolf of steal 1.02 and it have a patch 5, you can overwrite.
Every other time what you can do is compare the files 1 bye 1 to the other mod it wants to overwrite. If you are lucky there are only files you can edit with notepad. I use total commander compare function to see what the difference is and "merge" them, ofc if you know what you are doing.
of course you don't ,I don't either TDW knows , we don't
So you have 2 option: Wolf of Steal or Sobers mod list.
I myself use WoS and added a few things I liked and COULD with the merge technician I mentioned above.
Now I get a CDT every hour
so I will go back to pure WoS