Really appreciate the input guys, thank you!
Here’s what I’m thinking right now:
1. Standard GP Premium – $39.95 one time fee, up to 5 sites license key activation limit, your own websites only.
2. Agency GP Premium – $xx yearly fee, renewed at 50% off. Unlimited license key activation limit, your own websites and client sites. White labeling option + ability to add license key and activate GP Premium add-ons via wp-config.php.
This way, small business owners/hobby site owners don’t have to worry about yearly fees – hardly anything changes.
Agencies/web developers who make money off of GP Premium do their part in supporting it annually, ensuring that it remains profitable and awesome.
As always, feedback is welcome. This is just something I came up with on my evening walk 🙂