I contacted support and they sent me a very general e-mail, and it was enough to walk me through the process. In case anyone else experiences this issue and needs some additional details, here are the instructions:
Since you had packages, after you did factory reset packages settings remained, so that might be the reason you had issues. Let's just do a clean installation.
Here's how to connect via console https://portal.pfsense.org/docs/manuals/reference/sg-series-serial-console.html
Since you're using OS X, all you need is the command like this: screen /dev/cu.SLAB_USBtoUART 115200 (try it first, before installing drivers, if it doesn't work then install drivers from the link above).
To reinstall pfSense, simply login to portal.pfsense.org and under USB Memstick Installer download the latest 2.2.5 ADI Netgate image. After you download the image, flash it to USB. Here's the guide on how to flash image to USB from OS X. https://doc.pfsense.org/index.php/Writing_Disk_Images#Writing_Images_in_Mac_OS_X (click expand).
After that plug in the USB to your 2220, connect console cable and power cycle the unit. USB will boot first into setup wizard. From there, select Quick / Easy setup and follow the wizard. After that installation will be complete.