I have been around aviation all my life, but I am the first in my family to actually be a pilot or be involved in the industry.
When I was 12 years old, I took my first ride in a T-6 Texan, the pilot told me multiple times how shocked he was when I took over the controls and that he had never seen someone as young as me be so smooth. When I started flying towards my license, the same thing was said by my instructor. And I have even been complemented by my designated examiners during and after my checkrides.
I soloed in under five hours, I completed my Private training in 36hrs (pt 141). With the exception of my Instrument Training, I completed everything under mins and had to fly just to build time to meet requirements. Even in the case of my Tailwheel endorsement, I was ready for my sign off in ~5hrs but flew with the instructor until 10 to reach insurance Mins.
When I started flying jumpers, before I even got into a plane, they told me they would have me fly the 182 for a couple of weeks to get used to the type of flying. I flew the 182 checkout (already had time in 182's) and they put me on my first loads that night. Halfway through the next day they came up to me and said your fine in the 182, we are going put you in the 206 if you think you are ready for it and so I started flying it.
Am I Confident in my flying? Absolutely, if you are not confident in yourself, then you should not be flying, but at the same time I know I can still kill myself and others if I Screw up. I am highly critical of myself and I recognize when I should/could have performed better. I don't want to be hired and just set free at some company. I want to be trained in the aircraft as I know I have to be as part of the learning experience.
I also know that there are areas in my flying where I am not proficient in. Because of that, I stay away from those operations unless I have A) done a refresher on the areas or B) have someone else there with me who is more current than me.
My confidence comes from people who I have flown with as mentors/Instructors, not something I think up about myself. When you have multiple retired Air Force pilots and career airline pilots telling you good things about your flying, what do you want me to say? "Oh I wish you would hire me for my average to below average flying skills/knowledge."
Do I think I know everything? Absolutely not, I am continuously learning new things about flying and aviation in general. When I read for fun, it's about Aviation because maybe one day when the **** hits the fan, something I have read in the past will rear itself up and allow me to overcome the situation. If you were to ask someone what my interests are, everyone would say Aviation and nothing else because I surround myself in it. It is my passion and some would say my life revolves around it, which it probably does.
Here is an issue I have about people saying "Oh you only have X amount of hours. You don't have any experience or hardly know anything." Numbers do not mean anything, it's about the type of environment and the quality of the training/hours. If numbers are what determines experience and competence, then why did Asiana 214 crash? Considering there was over 22,000 hrs of experience at the controls and even more sitting behind them, yet they couldn't do a basic visual approach without stalling the aircraft.
As far as the aircraft I have flown goes, a lot of them built on top of one another so it's not like it's a huge leap from one aircraft to the next. example 172->182->206. I should have said 14 different frames, as it is only 10 different type certificates.
And you surely are not saying it should take someone 500hrs to become proficient in a single engine aircraft are you?