I recently (mostly) finished a legacy data migration and here's my advice: Treat it like you would treat a climbing expedition on one of the world's dangerous peaks. It's a given that failure is more likely than success; in fact it's potentially worst-case-scenario catastrophic. You will encounter many optimists along the way, and these are your most dangerous enemies - get them off your team ASAP. The people you can trust are the pessimists who insist on double-checking every assumption (how old is that rope?) and worrying about the what-if's. If folks can't accept your "attitude problem", walk away.
My organization narrowly avoided a business-crushing event a few months ago. Years of optimistic promises were finally put to rest and the sobering reality came to light: our legacy migration is, at best, going to be done in 3-5 years.
We were just barely within the window to order a pair of new servers before the Itanium order book closed forever. Naturally, our old servers are too old for VSI to support, so HP was willing to sell us a license to give us time to migrate from the old legacy servers to the new legacy servers. It came with a warning that THIS IS THE LAST OPENVMS LICENSE YOU WILL EVER GET FROM HP AND YOUR CEO MUST SIGN THIS BEFORE WE GIVE IT TO YOU.
http://www.pvv.org/~roart/freevms.html https://github.com/rroart/freevms