I'd probably do each flight as I saw it.
This is the painful part of the simulation. I start flying known flights over known places. I then meet other known flights in which I have been as a passenger in real life (I am not a real life pilot). I want to fly those as well. I reach known destinations and I see known airport structures (it's never enough) and there come the simulation limits: you cannot see real airport personnel, real people living around airport etc. I think I am already obsessed...
The funniest thing is that I had no interest at all for FS about 6 months ago and now I spend hours daily...