As Skogs pointed out, a perfect vacuum is a good insulator. Meggering across a less than perfect vacuum can cause flash-overs and if the test voltage is high enough, X-rays.
Also, the OP was about meggering HVAC equipment and transformers. Two examples where the term "Vacuum" may mean a reduced pressure that is susceptible to flash-over rather than a perfect vacuum.
Bill
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"Why not the best?"
Jimmy Carter