Hi Doug, #1 is using TuneIn. #2 engages the full-featured BiggerPockets and BiggerPockets Money skills. The issue with #1 is likely because there are 3 different versions of BiggerPockets out on TuneIn.
As a tip, you can get to the custom BiggerPockets / BiggerPockets Money skills directly by just saying "Alexa, open BiggerPockets" or "Alexa, open BiggerPockets Money".
Let me know if you run into any issues with the custom BiggerPockets / BiggerPockets Money skills.