"On the other hand, changing my business card to "Janitor," driving an old car and relying solely on my wit, charm and good looks only got me dozens of dates.
I enjoyed the ladies from group 2 infinitely more."

 Thats because group 2 really likes you for who you are. They aren't superficial, looking for more shoe money. Most guys have a hard time getting beat up on the way, suffering rejection,trying to find a woman that likes their personality .
If not for superficial women, new car sales would be close to nil.


 

In my mid 20's when I was homeless and worked at barley above minimum wage I had next to zero women interested in me then. Please note I still bathed daily and wore clean clothes. Now that I am much better off on the rare occasions I dress like someone in my income class bracket I have women approaching me. I am still just as ugly and fat (well almost) as ever. Women like money and the appearance of money but that is not new. Since I am rarely caring what most other people think and am not looking to pick up civie women I generally dress blue-collar as it fits who I am. It is fun sometimes to dress up an have the women notice me if only for the fact I look like I have money.

Money, the appearance of money or the potential to make money=confidence=women.    Simple equation.