While Pittsburgh is owned by FSG, they're not exactly known as being high-spending teams when it comes to the front office. Dubas is all in on analytics which aligns with ownership. He could go on a three-year vacation in the Bahamas and still have his job.
At the time of the Karlsson trade, the thought was this would make them a playoff contender. By the deadline, they were a few points out and Guentzel is a pending UFA. The fact they prioritized prospects over picks suggests they're not moving off the win-now (or soon) approach but knew there was a good chance Guentzel was leaving for nothing in free agency so they opted to sell.
Yep. 12 wins the first lottery. That locks SJ at 1 and 12 moves up to 2. Whoever wins the second lottery gets 3, hence the miniscule odds.