How many times can you reapply sun cushion?

I get blemishes really easily, and

I have skin that tans easily.

So when I go outside, I can't help but obsess over sun care.

The stick is

Applying over makeup

It was difficult, so I bought a sun cushion. Even with a sun cushion, how many times can you reapply it...? What about you?

For me, reapplying it repeatedly feels stuffy and leaves a bit of a greasy feeling.

Please let me know if you use sun cushions! Even if you don't use a sun cushion, please share any tips you have for reapplying sunscreen.