"We bring him a bottle of wine."
Translation:Gli portiamo una bottiglia di vino.
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"Lo" is not acceptable here because it is a direct pronoun that answers the questions "Chi? che cosa?" (whom? what?)" , while "gli" is an indirect pronoun that answers the questions "A chi? A che cosa?" (to whom? to what?)"
- Lo = him
- gli = a lui = to him
for more explanations and examples check http://www.cyberitalian.com/en/html/gra_prpr.html
As someone that has been through the Spanish tree and practiced for a few years, you'll feel that way for a little bit longer.
It's challenging to introduce a language, because the easy introductions to get you familiar is not how the language is commonly used. So you kind of just have to accept that the basic structures you've learned so far are going to fall away, to be replaced by more advanced (and commonly used) rules/forms.
It's frustrating but understand this: you probably don't remember being frustrated when you learned English as a child.