Thanks James, Zed, Kevin and Filipe. This is really valuable input and I hope it helps others besides just me from the archives someday!

I talked with the CEO yesterday more about this yesterday. I think we were able to "level" his expectations about what's possible vs. what's reasonable, affordable and not too risky.

Surprisingly in this company, the DBA/IT and programmer guys would love to abandon their current systems: stored procs, IIS and the whole MS house of cards. I guess that shows you how bad the rig is there. The system is so old that no one at the company understands how it really works and would all just as soon bury it if they could.

But from all your input (which jibes with my concerns), I think it would prohibitively expensive to try to shut down the existing infrastructure and write a new white box system, especially outside their current MS systems.

They can probably milk their existing infrastructure for some good profits for a few more years, if they can get people who will actually work and learn on it. (Any ideas on how to find folks who are competent AND willing to work on old systems? Outsource maybe?!)

Thanks again for all the insights.

Steve

p.s. Maybe I'll see some of you at Railsconf? I'm giving a talk on Search strategies in Rails on Friday 5/30 - afternoon sessions. Stop by and say hi!

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