No, I'm not mixing up anything. I'll generate 3.3V PWM, then level shift it up to 5V (still PWM), then filter it to DC so I'll have 0-5VDC out (roughly, not exactly, but close enough).
Then you're making it FAR more complicated than you need to - all you need is a simple NPN transistor (or n-channel FET) and a collector/drain pullup resistor to 5V. This will invert the PWM though, but you should be able to invert that in the settings for the PWM hardware, which is why it's there.