[bogwog]

I don't remember what the first software I purchased was, but after that point, I no longer was hesitant to spend money on good software. In hindsight, it was an irrational fear (maybe "fear" isn't the right word though). I'm not even a cheap person, I just always felt wrong paying money for any software that wasn't a video game. I wouldnt even buy dirt cheap mobile apps.

The only exception nowadays is subscriptions. I avoid those wherever I can, and will happily buy a more expensive/inferior alternative rather than pay a subscription. That might be irrational too, but I can't shake the feeling that I'm being ripped off and/or exploited any time I need to pay for a subscription.