We have done it several times, with global entry you scream through at SAN as few pure leisure travelers seem to have it and the go back to wait for the PDX departure. But last spring and again today just booked for January on the PDX/PVR non-stop. It gets in two hours later going down but leaves at a more hospitable hour about 10am vs. 6:30. Coming back it leaves about 30 mins later than the SAN flight but is in PDX about 5 hours later, way earlier than the connection. Why not take that flight (it does only run for days a week).