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Although I don't notice a lot of the nuances you do, I'll give it a try:
Have you ever met an Elena? How did she pronounce it? never met one.
How would you pronounce Elena? Uh-LAY-nuh
How would you pronounce Helena? Huh-LAY-nuh
Have you ever met a Helena and how did she pronounce it? Huh-LAY-nuh.
How do you pronounce Alaina, Elaina? uh-LAY-nuh.
Have you ever met an Alaina, Elaina and how did they pronounce it? same way I just said.