Yep. I suspect it's kind of both like most things
Caffeine does increase your TDEE, so it does help with losing weight. However, it's not a huge amount by any stretch; approximately 1 calorie per mg of caffeine. So that would mean 1 large cup of coffee each day would be about a pound a month of weight loss. Not a terrible amount, but not a huge amount either. It also helps with focus and gives energy, both of which are usually good.
However, it can also lead to heart palpitations, higher blood pressure and other bad stuff. The more you drink, the more this can happen. Obviously adding sugar, heavy cream, etc is going to lead to more calories, which will undo the calories burned from the first paragraph.
tl;dr: drinking 1-3 cups a day is fine, particularly if you don't add in sugar and other crap