I use SkyTools 3 Pro for planning an observing session and plotting star charts. I find the interface very easy to use and the interactive atlas has the best looking visual appearance of any other astro software in my opinion and I have bought and tried quite a few others. There are also naked eye, finder and eyepiece views for any telescope/eyepiece that you may own. The images may be flipped up/down or mirrored left/right if needed to match your telescope view.
Look at
http://www.skyhound.com/features.html for a feature list. Note the Pro edition has the realtime option, many more stars and features for imagers and is well worth it in my opinion.
My favourite feature is the Nightly Observing List Generator which with a single click can offer you a choice of observing lists, eg, Showpieces, Deep Sky, Double Stars, NGC, Less Known and a few others. Another click and an observing list is generated. You can also generate observing lists based on custom criteria or download observing lists for well known books such as Burnham's Celestial Handbook and many others.
Once you have your list you can then click on individual items on your list and generate finder charts to locate each object at any scale you wish. When you click on an object on your list you get a graphical representation of the path of the object at your local site as well as the path of the Sun, Moon, twilight and period of darkness for best viewing. The optimal time for each object is listed in a column on your report along with many other observing parameters. See screenshots on publisher web site.
I do not use GOTO or do imaging so I cannot comment on any features associated with these topics but SkyTool3 Pro well caters for such scenarios. It is the best astro software I have invested in and I highly recommend it and if you can afford it get the Pro version.
(Amended this para after discovering new feature).
If there are any cons it is that the virtual sky (naked eye) planetarium mode is not as pretty as Stellarium but it does show what is up above your local horizon. I still use Stellarium for a planetarium view for times when I want to check general positions of planets and the Moon on the west or east horizons. Prior to getting ST3, I got The Sky 6 Pro but I much prefer the ST3 Pro/Stellarium combo for all my astro software needs as the planning features of ST3 Pro are much better and the charts in ST3 Pro are simply stunning both on screen and printed.