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>FR/LG
>not being full of hand holding
please, these games were so hand-holdy that they had to tone it down in later games
Honestly, Black/White fit the bill for what you are asking for perfectly, and is designed as a re-introduction to the series but for what might be a critical flaw, in that it only has Gen V Pokemon (a personal upside, but I know where you're coming from)
X/Y, despite being generally disparaged round these parts, are probably your best option. They feature a wide assortment of Pokemon, and are heavier in Gen 1 Pokemon that she is familiar with, but not to the point of excluding newer stuff. Features like dressing up your trainer and Pokemon Amie are severely undervalued, and can really help draw people in that otherwise wouldn't play the games. They're definitely the prettiest games in the series (ORAS environments suck). The plot is kind of stupid but lets be real, that's not something you're avoiding by giving her any other Pokemon game.
This isn't even considering all of the general quality of life updates that the series has had, like re-usable TMs, faster movement speed, less HM requirements, easier access to hold items that make a difference, etc.
Plus, if she likes these games and wants to move on to Sun/Moon, transferring her favorite Pokemon over isn't going to be a bitch and a half.