Terry took the words right out of my mouth. Tell him to bring a change of clothes three days a week as he will be on the shop floor all afternoon. Hold his feet to the fire and make him bring industry publications and catalogs home with him to read each night and while he's on the toilet. Helped a buddy of mine get a business off the ground once and the manfuacturers we rep'd couldnt understand how we knew their product lines better than them and so fast and its because the two of us would read the product catalogs like a book. Taking apart part numbers and understanding the breakdown so it became a second language. He will have to do that with the software, the design process, the installation process, and the manufacturing process.
There is no YouTube playlist that is going to bring him up to speed in a few hours of watching though any videos beyond the hobby realm may be fine (if you can find anything).
It can surely work. That said, even any of the best emplyoees Ive ever had have never immersed themselves in the process like I outlined above. Ive often though that when I find that albino deer in the woods I will give him/her my entire business and sit back and take a small percentage. Needless to say Im still working.