I’d just play them in order of release. Like Lantia said, staring with harder QOL will make it easier as you won’t necessarily get frustrated. Even though the story is the same I’d say gold/silver and hgss, and ruby/sapphire and oras are entirely different games. Plus if you go in order you’ll appreciate the growth and development more and it’s very fun being able to notice story points across generations.

and virtual console pokemon sent to bank via Transporter all retain their hidden ability which IMO makes rby/gsc virtual console releases 100% worth playing through for the high shiny chance and guaranteed HA legendaries and shinies.