Do not have direct experience with commerical software.
I use/have used the free tool CNebulaX which is a little different. It is not small when you down load all the data bases including the >100MB guide star catalogue with 25 million plus stars in it. Full installation cost me about 361MB disk space.
It has planning components to it allowing the building of observing lists, incorporation of notes, pictures etc.
Link:
http://www.uv.es/jrtorres/index.html and follow link at the top to CNebulaX.
Note that CNebulaX was used to produce the excellent Tri-Atlas series of maps (new version out soon).
While not planning tools, I compliment CNebulaX with
Cartes du Ciel (CdC):
http://www.ap-i.net/skychart/ which can get big when one incorporates a number of catalogues. Installation with far too many catalogues: 701MB.
StarCalc (
http://www.relex.ru/~zalex/main.htm) with a few extras including 32MB Tycho catalogue and the GCVS for a total of about 68MB.
You can interface the USNO catalogue into CdC or StarCalc but it will cost you about 5.9GB of hard disk space.
There are other packages out there such as HNSky, Stellarium etc.
There are a number of sites that give links to astronomy related software, one such starting point is:
http://www.pierpaoloricci.it/index_eng.htm
There might be further information on planning software there as both freeware, shareware and commercial are linked.
There is also some discussion in another forum with regards to observation logging software. Deviates from your planning comment.