There was a running joke in my old game group. I would always buy Buffalo-Rochester as my firt purchase every game and as if by magic it would be pulled for proffit almost every turn, it was great!
I usually do my damndest to secure the north-east, JFK, DCA, DET and always play Orange because "We always fly high at SkyHigh!
one of the guys I would play with would always buy West Palm and then San Antonio. Every game (provided he had the money). There were some game nights he was running late, we played his first two moves for him and he ended up getting paid on all his chits before he showed up!