> Awesome! What is your extension?

It's still under wraps but I'd be happy to compare experiences when I launch.

> I did look at in-app payments, but because of how the extension is made to be used (click the button, it starts reloading when required) I couldn't figure out a decent way to ask users to upgrade without being annoying.

Hmm, maybe by default when you click the button make it show the config pop-up you have already with an added upgrade banner. You could add an option to not show the config pop-up on click as well.

I have no figures to back this up but unless you're a well known brand I think not having a completely free version to try will turn away a lot of potential sales. You say in your post you had a noticeable drop in the web store charts after making it a paid app.

> I went for subscription because I wanted a low price point (It's a simple extension, anything more then $5 seemed like I'd be asking to much), with the potential of having a passive income. I'd love to experiment with how one-off/monthly changes the amount of sales but for now I'm happy asking people to pay yearly.

I'd avoid equating code complexity with how much you charge. Charge by how much value your extension brings to customers. If it's saving a freelancer X number of hours per month then that's worth something more than the number of lines of code it took to write. Live reload is a big productivity boost.

By the way, did you look into experimenting with price changes? Since I last looked, you can easily change the in-app purchase price but you can't with subscriptions. I think the only option for the latter is to create new subscription IDs for each price.

Regarding the subscription: this would be a huge turn off for me. I guess I disagree with the price model, so I'd only get into a recurring cost for something I deemed essential, whereas I'd be much more likely to pay a (similarly?) small sum as a once off. This isn't criticism, just opening the possibility that sales might be a lot higher as a once off, and if you end up rewriting/adding a tonne of features you could always release V2. I'd be curious how many years an average paying user would actually end up using/paying for with a tool like this.

Obviously this is purely anecdotal, and this extension isn't applicable to me personally anyway.