Comments
I occasionally donate to user-funded services, but it is very ad-hoc and not a lot of thought goes into deciding which ones. I think I donated to Wikipedia a few years ago, and I donated to a local public radio station once. It usually happens after I use a service for awhile and suddenly think "hmm, I want the people who make that to know I appreciate their service."
I don't think it's ever been anything more than $20. And again, no rigorous decision making process, something about $20 just seems right as an "appreciation donation." The dollar amount might go higher if I ever encountered a user-funded service that I believed needed more from me to stay afloat.
I don't donate to any of them. I wonder if I should be more utilitarian by not tipping at restaurants and other things along those lines.
The cases i can think of to donate to these services would be along these 3 lines:
I'm open to argument 1. I do think stuff I've read online and podcasts I've listened too have been enormously important in my life.
That said I'd think about the marginal impact of my donation. If I thought X podcaster really needed the money to continue podcasting I'd consider donating to them. If the podcaster was already really successful and I didn't think they'd use my money well then I'd be less likely to donate to them.
I also think argument 2 is valid, though I'm skeptical that any service which helps you take a break is the best cause.
I don't like my third argument, but I think there are plenty of effective altruists who would endorse it.
To add on to your thoughts about argument 2: even if taking breaks with X podcaster is crucial to your personal productivity, you should still ask yourself whether X podcaster needs your money to continue podcasting. And then even if you decide they don't need your money to continue, but you really want those fuzzies from donating to X podcaster, then remember to purchase fuzzies and utilons separately.