Of all the quest cards released to date, this looks the most difficult to complete. In addition, trying to complete it makes things more difficult on your team. However, here are two things to consider:
1: You can coordinate with your team to try to achieve this in a round or two where very few tests are taken. It's pretty rare that any scenario gives you a round or two to spare, but getting your allies to take as few tests as possible while you focus on this gives you a decent chance of succeeding.
2: This will probably flip easiest in a 4-player game, where your allies can also add curse tokens to the bag. From the preview cards we've seen, it looks like some classes will be better at adding curses than others, so your mileage will vary. Still, getting a boost from your teammates will certainly speed things up.
In conclusion, combining these concepts should make flipping this pretty consistent. Thank you.