You don't mention the language or regex engine that you are using, but going by the error message, some regex engines only allow fixed length look-behinds. Now each of the alternate paths you have are fixed length, but together they could be 7 or 8 characters long. this is a possible cause for your error.
If you have a regex engine that can handle lookbehind, you will also be able to use lookahead. Most regex's that allow lookahead also allow variable length lookahead patterns, so perhaps something like (untested):
coolguy/most/(?!.*?(test|man)\d{4}).*
may work.
Susan