Quebec can enter the US via treaty just like Texas, since it was once independent (Nouvelle-France). As for timing, I think everyone has agreed to wait until Queen Elizabeth dies and the pedovore stuff of the royals comes out.
The rest of Canada? Ontario and BC can be states, the Prairie Provinces as one state, and the Atlantic provinces as one state. The North can be annexed to Alaska.
Five states = ten senators and about 50 house reps.