Hi YYZFlyer,

Thanks to the suggestions and ideas.

I had been looking at the following:
1) CO CLE-MSY-CLE and CLE-LAS-CLE
2) CO CLE-MSY-CLE and CLE-SJC/SFO-CLE and WN SJC-LAS-SJC
3) NW flight / Milage run to maximize Miles and chance of upgrade.
4) AA Milage run to qualify for Promos and maybe do an Elite challenge since I have been having sufficient problems with AC to write a complaint letter to Robert Milton!

Contraints - don't have much time on Feb 13, more on weekend of Feb 20-22, may not have much time on Feb 25 either. It is 2 trips but since I have a weekend in between I can try them in combination or separately.

Normally I either pay a bit more for the convienience of direct / short flights or stay with my perferred carriers without paying for outrageous fares if I am short on time. Whereas when I have some flexibility and time, I go for the better price / benefit routing or to hit significant bonuses. Unfortunately this has elements of both but I am being tempted by AA promos such as AANYC, AABOS, FLY04, and Elite Challenges (uhmm possible refugee from Air Canada AP)