I went with option 2 and tried variations of option 1. Option 1 has worked better.
If any of you purchased the Continuity Blueprint, this is something that Ryan Deiss discusses as well. A low price front end and continuity. Then upsell a larger package or more features.
I've just reach capacity for my first season of coaching on my program, but plan on going back to option 1 with the next release in a month or so.