I hope you won't mind me resurrecting this thread, if only for "cultural" purposes...
First, licences:
A "regular" Canadian CPL gives day and night VFR, plus VFR OTT privileges with the ability of flying for hire.
Things you can add on it: float-rating, multi-engine rating, instructor rating (a single rating with four different classes allowing you to before chief-flight instructor and to eventually train new instructors), IFR (group 3 single-engine, 2 centreline thrust, 1 normal multi), IATRA exam (which enables you to fly "high performance" aircraft, here meaning Vne >= 250 KIAS or Vso >= 80 KIAS that require a type rating, not to be confused with a CARs part VII Pilot Proficiency Check a.k.a PPC.)
A "regular" FAA CPL gives day and night VFR privileges with the ability of flying for hire. Without a valid IFR you are not allowed to carry passenger on cross-country flight of more than 50 nautical miles or at night. No such thing as a VFR OTT rating in the US afaik.
Things you can add on it: float rating, multi-engine rating, the different instructor ratings, IFR, tailwheel endorsement, high-performance endorsement (engine over 200hp), complex endorsement (flaps, retractable landing gear, constant-speed prop). The last three don't have any equivalent in Canada, matter of fact the concept of logbook endorsements was entirely foreign to me before I got my FAA certificate. (Sure we might sign the hours in a logbook, but that's pretty much it.)
Second, single engine IFR commercial operations:
As explained by Rooster Cruiser, you can fly a single engine piston for IFR on demand charter (part 135) in the US whereas you can't in Canada under a part 703 commercial operators certificate.
Canadian rules for night VFR and IFR under 703 require either a twin or a factory built single engine turbine airplane with a minimum proven MTBF of 1 failure in 100000 hours or less.
So a Caravan, PC-12, TBM or Meridian would all qualify, but not an STC re-engined PT-6 Turbo Beaver or a TPE311 engined Caravan for instance. (See CARs
703.22 and
723.22 for more)
About jurisdiction, you pretty much fly under both set of rules. If you're *really* in a bind, the Chicago convention might have more answers...
Goodbye,
Louis