You know that you're probably going to be with the trainer for the duration of the project, so pick someone with whom you're comfortable. Look for things that set the vendor apart. Ask for references and use specific questions, such as whether the vendor met deadlines and stayed within the budget. Focus on the things you respect in a vendor. Make sure that you're comfortable that your vendor believes in the same values you do.
Functionality is the most crucial evaluation criteria for courseware.
If courseware is marketed to a particular industry, then the training team should expect the vendors to explain where and how it fits in. Since most software training is competency-based, it's easy to make the courseware technically accurate but very unfriendly. Each piece of courseware must meet certain minimal conditions. It should be modular and consist of a series of lessons, where each section covers an area of the product. Because the manuals and training material are what students will have sitting on their desks after the class, they must be easy to reference quickly.