yyzflyer,

Thanks for the welcome.

MSY and LAS dates have a weekend in between so can be
1) separate trips out of CLE
2) onward travel - but then what do I do with the weekend - NYC, SFO, LAX or LAS
3) milage run in between
4) convoluted routing for both to do promo, milage run, and challenge.

Yeah, YOW is not great for flying out of, most US airlines use little prop planes or small regional jets...