Doubly na Kanojo ~H na Jonan ka Dou ka wa Sateoki~

The protagonist's life has been nothing but disaster.
The fiascos he encounters are always woman-related.

Indeed, he has "girl problems".

Every time he meets one it's another wild ride.

"Here let me take off your pants" = problem
Girl wanking him with her hands = problem
Girl in sexy school swimsuit = problem
Maid uniforms and cheerleaders = problem

Sounds like one of them good problems to me!

[from DLsite English]