Wondering about beverage calories

Hi!
Wondering how strict you guys are on logging drink calories? I log things like smoothies and frappes, but that's really it.
Is it imperative to track my calorie intake from things like milk, fruit juice, and fat-free creamer in my coffee to achieve my weight loss goal in my allotted time?

I'll appreciate any advice! Thanks!!

I used to think of skim milk as "water: with bonus calcium and protein!" (I grew up in a "low fat = healthy" family.)

Then I started counting calories and realized how much my milk consumption was adding up. It makes a big difference! Especially when all my glasses are pint glasses -- so I'm usually drinking 1.5-2 servings instead of 1 unless I measure (which I always do now!)
Most mugs and glasses these days are 12-16 oz, not 8 oz.