It seems that COBOL is the main addiction that makes you worry. I undrestand Itanium + OpenVMS in this figure - it's just a platform.
At OpenVMS, you are definitely not alone in doing critical things. The HP website has an open OpenVMS card (both Alpha and Integrity), support is currently stretched until 2015. Oracle seems to be trying recently to use its SUN asset across domains.
In any case, if your worries are significant (I’m sure that we all worried about COMPAQ, then HP, vax → alpha → Itanium goes over in the past), there is time to undo the COBOL dependency.
So, now I will consider the migration path from COBOL to a more convenient language (for example, C / C ++ ANSII without platform extensions). Java may not be the preferred choice given Oracle's activity. Repeated recording, as it is unpleasant, will be more progressive and, most likely, will simplify the whole process. The sooner it starts, the sooner it will end.
In addition, there are still a lot of used equipment in addition to emulators. Ironically, one company that I only know now is on Integrity platforms, to supplant critical versions for Alpha - I think these are “corporate testing requirements” ...
Do-nothing is also an option, although obviously more risky: OpenVMS platforms have proven to be reliable, so alternatively looking for a reliable third-party support company can extend your future hardware.
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