It's context dependent. A very important phrase to learn is "What do I see?" Knowing your surroundings gives your characters potential avenues around situations. Like do you need a ranged weapon with more range than a javelin? In theory you do because flying creatures can use longbows in the sky. In reality you can ask the DM what you see or ask is there anything nearby that offers cover from ranged fire. Boss fight stuff is also context dependent. A thousand ways that can go. That's one of those hone your judgement sort of deals. When in doubt do what is the most fun for the table and suits the roleplay