This has sometimes been my experience too. I've been with Linux Mint the last 4 years at home, doing pretty much the same set of typical home PC tasks: Reading the paper, youtube, fb, gmail, banking, watching movies, managing photos, home videos the kid's homework etc.
After doing it for 2 years, I felt I'd been through whatever Linux Mint could throw at me and I actually started recommending it to a few friends, touting it as a no-cost alternative that would be worth trying. Even the local kindergarten needed 2-3 better (and cheap) PC-system for the next 2-3 years for their occasional office computing needs. They were really impressed.
Then it dawned on me.
The people I know who are now on LM:
1. Are more willing (and expecting) to be able to pay for better applications can now maybe get 10% of their wishes granted that way.
2. Are willing to and expecting to call someone and give them $50 to fix stuff. (They can only call me as there are no other Linux guys)
The point is that the money is there for you, it's just very hard (practically) for people to spend it.
Take donations for instance: This is money that you give to the developer *after* you have downloaded and used some application. Only a small fraction of people even remembers to do this.
In many cases you can only donate to some foundation and then only hope that this goes towards developing that one feature you need.