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Definitely book those island transfers as soon as your resort is confirmed, especially if it's peak season, they can fill up and you don't want to be stuck on the mainland.
You have to be online the moment the bookings open for the season and be quick, or look for cancellations closer to your travel date as people's plans change.
The Metro is better than Uber for rush hour travel. Traffic in Santiago gets absolutely insane, so the subway is the only way to guarantee a fast trip during peak times.
Recoleta is great for sightseeing because of the architecture and proximity to the cemetery, but if you want more authentic restaurants and a slightly younger crowd, I'd choose Palermo Soho or Hollywood.