I see this as two separate, though related issues. One is passing on the craftsman skills and experience, the other being the "book knowledge". Many of the railroad museums have libraries which contain a wealth of information. This can include old ICS (International Correspondence School) courses, manufacturers drawings, and so on. The problem is that many of these collections have never been properly cataloged, making it near impossible to find the material. Even when cataloged, there still needs to be a means to allow for easy access to folks
outside of the individual museum or library to access the catalog.
We need a concerted effort to instill a desire within these disparate organizations to work together. Establishing the physical hardware/software is easy, and reasonably inexpensive. The problem is the huge amount of time required to catalog and enter the material. If a restoration crew in Colorado requires a reference that can be located in Illinois, it's not that difficult for a couple of team members to travel, consult the reference, and return with the required information. Digitizing is an ideal solution, and could be accomplished on a parallel track. At least we could establish a pattern of need and demand and apply some intelligence in determining the priorities for digitization!