Thanks for the feedback everyone. I have pulled the trigger and booked my flights. I tweaked my plans a bit to allow for a 12 hour stop in MSP as well as a 13 hour stop in SFO.
Viajero Joven: Don't think I didn't try for that PDX stopover. Unfortunately, there were no K fare seats available on flights that fit my schedule. Maybe next time as I always like to visit Oregon in order to sample the micro brews of my home state