One of the most difficult things to do when contracting is understanding the wants of the client. Most people are not thinking that they need to explicitly detail what they imagine the project to be.
I think they somehow feel that you can magically read their mind.
With this in mind you need to do everything in your power to understand exactly what they want. This means not only getting the "details" in writing but also spending time asking the what if's...
Try to get the thing working in your mind before signing any contracts. Also, most contractors are very comfortable with the language before they dive into a major project. I feel by what you have stated that
there are too many unknowns at this time. It seems like it is diffcult to find ISPs who will let you have access to Perl or a cgi-bin directory these days.
Most contractors have written so much code that they have their own library of subroutine skeletons and modules that they are very comfortable meeting a project deadline. I am not saying that the new programmer will
not be able to do it but the contractor new to the language should allow a forgiving buffer time.
The bottom line is KNOW what your customer wants and understand ALL of your limitations and don't try to pull a rabbit out of your hat. Then it may be a little easier. Good Luck.
Best Regards
Doug