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Maybe because "sempre que" is a fixed adverbial expression meaning "whenever": http://www.linguee.pt/portugues-ingles/traducao/sempre+que.html. I'm not a native.
We generally use the object pronouns "o" and "a" for people, but they can refer to objects. We generally prefer using demonstrative to refer to objects like "isso" "aquilo". Also, the verb smile induces you to think about a person. I should also add that we use ele and ela to refer to animals
I don't know of any web sources that discuss this, but I've got a couple of text books that do. My understanding is that in writing and formal speech, the oblique form "a" is used as the direct object. In normal spoken language, "ela" is used as the direct object.
From "Modern Portuguese - A Reference Grammar" (Mário A Perini, Yale University Press, 2002), page 392:
29.4 Object Pronouns in the Spoken Language: A Summary
-Third, "ele" (he), "ela" (she), "eles" (they, masc.) and "elas" (they, fem.) are used as objects, so that "o", "a", "os", "as" have entirely dropped from current use, except in a very few fixed expressions. Thus, one says
Encontrei ela no supermercado. I met her at the supermarket.
Acho que vou convidar eles também. I think I am going to invite them too.
The use of object pronouns described above is universal and not, as is sometimes said, restricted to so-called substandard or uncultured language. No Brazilian, of any social class, region, or degree of education, routinely says a sentence like "eu a vi" (I saw her), although they will employ it in writing.
From "Modern Brazilian Portuguese Grammar" (John Whitlam, Routledge, 2011), page 59:
7.3.3 Using third person pronouns in the spoken language
In the spoken language, the stressed forms of the third person pronouns (ele, ela, eles, elas) are not only used as subject pronouns and after prepositions as in the written language, they are also used as object pronouns, being placed after the verb in the noun-object position (like você(s) see 7.2.1 (ii)):
Eu vejo ela todo dia. I see her every day.
I asked my Portuguese friend at the Ravioli shop about this. She says that where she's from, they say "Eu vi a ela."
I'm not sure what's going on there; it looks like the preposition "a" is being used as some kind of direct object marker.
When I asked her about "Eu a vi", she scrunched up her nose, shook her head and said "No!"
Duolingo is accepting but remarking "everytime" as a typo.
It is in the list of "English disputed terms" of Wiktionary and is said to be an alternative spelling.