I know that the bounds of what is considered "personal" are different for each font creator. However- I want to know what the general public consensus of using a personal use font for a free game or the album art of a free album is. Would you personally consider that to be public, or commercial if
someone chose to pay for a pay-your-own-price game or album that was basically free?

To me that is no longer personal use even if it is not for commercial use.

Get in touch with the font author and fully disclose how you are going to use the font. In my case, I consider that you are acting in bad faith if you hide in generalities how you would actually use the font.