Even though I played Red, Blue, Yellow a LOT as a kid, I think compared to the later entries, it's very unhelpful. Items to learn moves are one use only. No run button (always needs to open item menu for bike instead of assigning it to select button), no idea what ANY of the moves does because it lacks description in game.
I recommend Fire Red/Leaf Green. They are remakes of the original Generation One games but you can also have the option to transfer them to the DS games (recommend Heart Gold/Soul Silver, remakes of Generation Two) and after that, get Black/White because that's the version that can let you transfer the DS Pokemons to the 3DS version via the Pokebank so you can finally get into the 3DS Pokemon and try out the X/Y which gives you a grasp of Pokemon in 3D.
Finally comes Alpha Sapphire and Omega Ruby, remakes of Generation 3 so in theory, you could transfer your GBA Pokemon all the way to the 3DS!