What factors influences investing experience?

[Adam Kasel]

I am just starting out in real estate investment. My first property will be, unless something changes, the duplex we're currently living in on a rent-to-own basis.

Whenever I tell people what my wife and I want to do we either get verbal support or some cautionary tale.

To those who have experience, what factors influence investment experience? Why do some love it and others see it as one of the worst mistakes they've ever made? Why do some succeed and others break even at best? Thanks in advance.