As someone who did the SK challenge, this seems way more difficult to accomplish and is significantly less rewarding. I put together an itinerary that has basically no repeat airports aside from SJU a few times and MCO once. This is theoretical though since some routes close at different times from September to November. In an absolutely perfect case scenario where it works, the price works out to $3500. Then I have to get to BOS and back from DTW and pay for overnight lodging for probably 7ish days since I'm utilizing Jetblue's network in a way it isn't designed to work. All-in, it would probably cost double what I paid for SK's challenge for 1/3rd the miles and an elite status with questionable value, so I'm probably out on this.