Since we're all different, the answer is different for everyone.
One thing we started doing on the EMS pilot side was gettin' rid of set time periods for new pilots to get comfortable. So say instead of a standard 2 weeks of flying with another pilot, just schedule the person to start flying with a partner and then whenever they say their comfortable, let 'em start flying cases on their own.
Even guys and gals who flew whole careers in the military needed some time to adjust to the single-pilot EMS stuff. And then adjust again to the single pilot IFR (flying in clouds) stuff.
I know it took me longer than "average" . . . if there is such a thing.
Sounds like you're doing great. Just the fact you care enough to ask is a good sign. I hope this helps.
Just as I start to get comfortable, I try to expand what I can do by taking more classes or certifications. As I felt comfortable as a basic, I started working as an Intermediate. I stayed intermediate past feeling comfortable and slipped well into being a medic. Now I'm having to get comfortable all over again with the expanded skills and expectations of having flight protocols on the ground