Great report, I love Sao Miguel and have made several trips - relatively easy from Europe with TAP and a connection at LIS. From ORD, if you want to go back, consider ORD-YYZ-PDL, Azores Airlines operates daily YYZ-PDL and their service is several notches above average and if you want to go to other islands once there, connections are pretty good.

Also, the links to car bookings from TAP's website tend to IME always deliver the most competitive deals. My next one is with Wayzor and they are good and pricing through TAP is better than direct.