I'd go with Anna. I love Lily (obviously) but Lily is in the top 20 now and when you add the popularity of Lillian, Liliana (which makes the top 100 when you count all spellings), Lilia (makes the top 1000), Lilith (makes the top 1000) and the various spellings of Lily that are popular as well (especially Lilly) the name is way too overused. I think most girls who are named Lillian, Liliana, Lilith etc go by Lily at least sometimes. It is possibly the most popular name of all, if you add all variants and consider all the girls who have a longer form but go by Lily.
I like Emilia, but it is easily confused with Amelia which is also common. I think she'd have a lot of 'No, not Amelia E-M-I-L-I-A.' situations. It's lovely, though.
I dislike the meaning of Leah and find the sound insubstantial. Julia is very 80s dated to me. I was born in the late 80s and know tons. Liliana is fine, but doesn't excite me.
While I do think Anna is also slightly 80s dated (I grew up with quite a few) it isn't very popular anymore and its popularity seems to be going down. Also it is easy to spell and pronounce.
If you love both Lily and Anna so much, have you considered Lilyanna (I think it looks sweeter than Liliana). Or maybe you should just go with Liliana because you get your favorite names, and two other favorites as nicknames. It might be the ideal solutions. LilianaEmilia is really nice.
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