How do you handle initial pricing, and increasing prices?

Hey friends,

I launched my frontend job board at https://frontendrocket.com 2 months ago, and just recently started selling job listings. I've started at $1 because I wanted to see if people were willing to pay anything at all.

I sold my first listing last week. I've had ~400 users visit the site last 30 days, and I have ~10 subscribers to my weekly remote jobs newsletter.

I plan on raising my price to $15 now.

Here's where I'm struggling / looking for advice:

1. Raising prices. In a situation like this, can there be backlash for raising prices? What's the best way to handle this? Should I say "introductory beta price is $X, later it'll be higher"? Can pricing too low hurt you?

2. I've considered giving 1-2 free listings at first. Any downsides to doing that?

3. I plan on offering a 30 day money back guarantee. Does this actually encourage purchasing? Anybody have experience with this?

4. How do you equate value for price? Is this just simply asking people how much they value your product?

5. Any good books / articles on pricing frameworks and how to think about this?

Any other general advice?