aco175
Legend
Now we are introducing masterwork picks or mithral picks as a mechanic. Players would want it to get around the penalty and other penalties would have the same thing like, instead of picks keeping breaking, maybe hinges make a lot of noise to alert the bad guys. Not I have oil and tell the DM every door that I'm oiling them.I presume that you would be a bit more creative than this, but let's just presume you're not feeling well and your creative juices are on empty. There are a bunch of locked doors I have to pick, and each time I get a complication my tools break. Around the second or third time that happens, I'd look at you and calmly ask if there's anywhere in your campaign world where I can purchase a set of tools that isn't made by Fisher Price. Because, IMO, it could easily get ridiculous pretty fast. PbtA partly gets around this by not requiring that the complication have any direct relationship to what you are doing (you're trying to pick the lock and something happens!) but, depending on your players, that might not go over as well in a D&D group. The expectations are different.
I'm not sure if a chart of failures would help with rolling a d10 and reroll for each failure that has been negated. I do not think that a masterwork pick tracking failures chart is good, but maybe advantage to a save from breaking. Not sure how big the rabbit hole would be.
Is there a simpler way to fail forward? Do you ask the player what happens? Is it just a time penalty to keep simple such as 10 minutes per point missed by.