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So lets pretend a character has a magic item such as a flying broom, or a flying carpet, or some other magic item that is shall we say obviously a threat to the monster they are currently fighting. If this giggling halfling is zipping around the place, tossing fireballs at the storm giant...

Not that I don't want the Rogue to roll all the dice on the table for a sneak attack, but I want to make sure he's not rolling all the dice on the table. So at level 3 Assassin with sneak attack: 2 D20 for advantage (unless he has a party member within five feet, and if the target hasn't moved...

So I'm new to being a DM for 5e. Second game and my druid learns the ability to turn himself into things. Namely a spider. Which he can use to act as a scout, all the time. He can also go into this form during combat and if he's hit just returns to his normal form. How do you DMs work this...