I'd do trancons. instead of segments.

West coast to the NYC area or BWI seems cheapest but last I checked they still seem to be around $.04 cpm, but then again, I am an not as experienced with MRs. Perhaps someone else can help you bring the cpm down.

To MCO is somewhat riskier as Hurricane (blank) can roll in...

Popular hubs seem to be DEN and ORD, so you might be able to route thru them to add some miles.