I have not tried to setup a new classicwb with 3.1.4 but i do use ClassicWB_68K on my CDTV and have upgraded the rom to 3.1.4
I was also getting the requester you're getting. What i did was
Insert the modules (mine i a cdtv i used the a500 modules disk) floppy and it loaded into workbench theni copied the icon.library and workbench.library file from the libs drawer on the modules disk to the main workbench installation libs drawer (so on my cdtv its in System:Libs). Now it boots straight in and doesn't prompt for any additional files.
on my list for tomorrow lol will let you know how I get on I think I might have messed it up first time because I copied everything from the modules disk to the cf
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