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Your graphic design is wonderful. What software do you use?  However, I have a little problem with the content. If I'm reading this right, there is a 2 in 6 chance you will get some kind of negative effect. Shadowdark classes are already not especially powerful, so to gimp them further, even if the possible benefits might be big (even, arguably overpowered, like 2 Tier 3 scrolls to start the game!) I think would make most of my players uninterested. And some of the negative effects are pretty terrible, like DC 18 to learn any new spells, I think I would be pretty frustrated as a player if my character started with such a big drawback.

Thank you, and it's Affinity Publisher! The cheap alternative to Adobe InDesign.
There are definitely some large boons and banes within the tables, but that's kind of the whole point. To give some extra twists and turns to a new character. Some players and GMs, especially those new to TTRPGs, may find it too much, which is completely understandable. This is very much something not designed to give a perfectly "balanced" or "fair" character, its more about creating a unique and different start to the game. I know  i enjoy having a few key moment/concepts to play a character around. Like a wizard that struggles to learn new spells, but deals double damage in rage at people that have injured them. And i think much like if you rolled a character's stats all 6's (or 18's), if your Life-Path was a bit too OP or debilitating, i would just roll it all again.