Hi,
Well first, have a staging database where you can test all your changes "risk free". It will allow you to do changes and determine best practices to upgrade your data. Since that is staging system, you can do it really risk free. Only risk is that you may lose some time but your production system is not affected at all.
Hopefully you do have QA team or at least good QA procedures to test your system before you can give a green light for your changes. Unit tests help in certain parts but they can't really tell that there aren't any bugs.
And there isn't really any shortcuts because only way to discover bugs is that something bad happens, you write a test to reproduce it and then fix it - there isn't really any way to tell if you have covered all potential issues with such a conversion before hand. It is guaranteed that you'll have some problems that you just happened to missed out. For example when doing math with dates DST changes may introduce interesting results.
And finally - you need to have a DRP - disaster recovery plan. So if things go really south you need to be prepared to handle it.