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Re: Tehlila should be spelled Tehilah, should it not?
I think that some of them feel a bit more natural to people because they are seen more often in one spelling than another. All of the name you have mentioned are Biblical (including Hadassah), so we see them romanized with the "h." Sara isn't as big of a deal for us because there are a ton of women that spell it without the "h."Having these names with the "h" keeps them more literal to the Hebrew spellings even if it is silent. So no, I don't think that it would be inconsequential.
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