Resource for learning how to read Jeppesen charts?

It’s a game. You can do as you wish.

But in reality, you always land and take off as into the wind as possible. Cross winds can be very dangerous, as can tail winds. They make the aircraft much harder to control.

Airports have runways laid out based on prevalent windws in that area, and the active runway is based on the wind direction at the time to give you as much of a headwind as possible.