My buddy is working on one that provides an API on top of Google Drive and can export a Doc to Markdown,

Thanks! Yeah, I think the Barter thing could be interesting. Curious to see how many people reach out regarding it.

About the number of plans, I’ve been struggling to figure out what makes sense. I want to display enough lower-priced plans to make it feel accessible, while still showing some higher-tiered plans to reinforce that it can scale with your team or project needs. But, I totally hear you, in this instance less could be more.

Freelancer by day and night (juggling two clients right now), and trying to work on personal projects when I get a free sec and can't look at client stuff.

LLC, just because it’s easier and can always be converted to a corp once you’re at that stage–assuming it makes sense for your company and how you want to structure it/handle taxes, etc.