Sgeirk,
You're probably right, having some support on hand might be a good idea, at least when trying something tricky like this... The folks at WO (Wide Orbit) are quite good, I'm told. Personally, I've been using the product from ss16 through to the GRA (Google v6) model, so I'm pretty familiar with it (good and bad), although I haven't had any personal contact with the new guys.
I just wanted to encourage him that it "was" possible to do a migration and point him in a direction. I generally don't have a need for support these days as my knowledge has been accumulated over the last 20 years or so.
Tech support for this sort of project will cost him a few hundred $$$... They'll walk him through everything and tell him everything he needs to know to do more than one system migration - it is quite more involved than the "reader's digest" version outlined above, just a synopsis of how it's done. A few hours on the phone at $100 an hour is well worth the investment though, when you think about how much mileage the system gets and the lasting effects of getting off of worn out hardware. There are several engineers who know what I've just told him, so it isn't top secret. If anything, I've probably forgotten something important and he'll need support anyway. WO is the best equipped to take care of him and I respect that. They are good at what they do.
Although I am working on my own endeavors, I have a lot of respect for where SS32 came from, and where it's going in the future. There are a lot of cool things ahead in the future of radio automation and WO will be right there, I'm sure.