I think that the first goal is totally dependent upon his current situation. It is very much a low hanging fruit scenario, so that grabbing the low fruit will provide some motivation and inspiration to continue one. Nothing worse than setting the bar too high, missing it and getting depressed about it.
It's not a low goal if you're just starting out, it's a realistic goal.
It takes time and triangulating over a lot of ideas before one gets good at coming up with passive income winners. I think the author is right on track and he has a great giver mcgiver attitude.
Also, the marriage proposal app is a pretty good idea FWIW.
The author mentions that he plans to set another goal once he reaches the $1,000 goal. My advice: definitely do so! It may not be easy, but it is possible. And yes, reaching an originally low goal may give you the motivation to continue.
My personal goal is to eventually have enough "now passive" income that if I were to lose my job, I could lower my standard of living and survive unemployed without dipping into my savings.