I use Stellarium to give me an insight in to what constellations are where. I then use NGC/IC Project's website to generate observing lists. I have built a spread sheet that can then take that data and present it to me in a printable A4, numerous pages, observing list by constellation. I then have a master register of what I've observed in NGC/IC/M order.
I can then take that and create say a Messier Marathon like I did for myself at the Ice in Space camp back in March.
I always find it a good idea to have a few sections of the sky covered. No point focussing North, for instance, if it's clouded out North but crystal clear South.
As others have said don't rush. If you have missed it this Winter/Autumn it will be back same time next year
Hope that helps.
Wayne