Goal Seting: 5 years of active investing with 300k in capital?

[Jefferson Smith]

For a relatively new investor with about 300k in capital, what would be a moderately aggressive goal for monthly revenue generation within five years? 

The general goal is to build up monthly passive-ish revenue within the next 5 years, and wealth generation for the long term. (I do nonprofit work, and I want build up revenue for my family and retirement that will allow continue to do service-oriented work.)

I am willing to be active and have a network of relationships. I am not a handyman, but I am a lawyer by training and I've helped with somewhat complicated deals before. I live in Portland, OR, where property values have risen significantly since the crash. My full-time job keeps me busy, so I will be doing this in the evenings and weekends. 

As I do goal setting, what are some realistic scenarios, benchmarks, and targets to help with the goal setting?