It's not immediately clear how this card interacts with Live and Learn. Does Drawing Thin apply to both attempts or just the first one? There was some debate about this, but the final ruling came from Matt Newman himself:
This is a bit of a tricky interaction, so I apologize for any confusion here. I agree it’s a bit ambiguous. I think the ruling that makes the most sense here is the following:
As a general rule, when you use Live and Learn to attempt a test a second time, all effects with a duration that expire at the end of the first attempt will have expired by the time the second begins. This includes effects used during the first attempt that say “until the end of the skill test…”, “…for this skill test,” or the bonuses from committed cards, which are all discarded at the end of the first attempt. Effects that are inherent to the test itself (the test’s parameters, what happens if you succeed/fail, that sort of thing) all remain the same, even if they have a duration of “for this test.” So, for example, if an effect said “play during a skill test. until the end of the skill test, increase the test’s difficulty by 2,” that would expire at the end of the first attempt, whereas if the test itself said “Fight. Increase the difficulty of this test by 2,” that increase in difficulty would exist in both the first and second attempts.
Now for the tricky part: Which is Drawing Thin? Is it an effect that initiates during a skill test with a duration of that expires at the end of the skill test? Or is it an effect which alters the inherent nature of the skill test itself, such that it would affect both attempts? Since Drawing Thin does not explicitly say any variation of “until the end of the skill test” or “for this skill test,” and since its triggering condition is a “when” reaction to the skill test initiating and not something you use during the first attempt, my ruling is that Drawing Thin is changing the skill test’s inherent difficulty to be 2 higher—altering the nature of the test itself. Therefore if you use Drawing Thin when the skill test initiates, and then use Live and Learn to attempt that test a second time, the increased difficulty would carry over to the second attempt.
Again, apologies for the trickiness/ambiguousness. Hopefully this clears up this interaction, as well as clearing up how Live and Learn works in general. Thank you for bringing this to my attention; I’ll be sure to add it in the next edition of the FAQ as well.