I use macro software to handle situations like this. For example, here is a sample AutoHotkey script:
::c1::chris.topher@hello.com
::c2::topher.chris@goodbye.com
::c3::chris@bla.com
::kr::kris@aha.com
When this script is running, type c1 and press the spacebar (or a punctuation mark or Enter). The typed letters will be deleted and replaced by the email address.
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