Be #1 on launch day or get 30 paying users right away?

From the perspective of long-term marketing of the product, I would lean towards the first option. However, if those 30 users are all high-value customers who make significant payments at once, that might just tempt me a bit hhh!

Thinking long-term, placing #1 on launch would definitely be the better choice. Sure you can guarantee 30 people paying $X - and that would be the easy choice for some. But if you can convince 300+ upvoters to get on a free plan, if your product is good enough, I'm sure you can convince more than 10% to upgrade to a paid plan pretty quickly..