I've been dabbling in content creation for several years and never put enough love into one thing long enough to watch it grow substantially. Before making videos (I have a fishing channel as well), I was really into podcasting. Prior to actually launching mine, I spent quite long time listening to a podcast about podcasting. He talks about all sorts of things like funding, partnering, advertising, audio, content planning, etc. MOST of what he talks about could be valuable cross-platform and applied to nearly all facets of content creation. The cast is called The Audacity to Podcast. He has hundreds of episodes but you can search by topic.
I only bring this up because he has an episode or two out there specifically around the sensitivity of asking subscribers for money, how/why/when to do it, etc. Good stuff. At the end of the day, it all boils down to value. If people find more value in what you're providing than what they're paying for (mostly free), they'll give you money for it. I would never expect anyone to pay to hear me talk about chopping up my neighbor's tree that wrecked my back yard fence lol.