The planning is almost as much fun as the observing sessions for me.
First of all I am limited in what I can observe. Geographically, I have a wide open view to the north and around to the east before the house comes into play. From due east to southwest I have the house to deal with. I have a good view to the south to about 5 degrees below Rigel and Sirius (roofline of garage). Unfortunately we live on the north side of town and there is serious light pollution to the south. Trees completely blockout from Southwest (about 200 degrees) all the way to almost due north (about 340 degrees). Second, my scope (ETX90RA) has limitations. Deep sky galaxies are out. Nebula (except for brighter ones) are difficult and globulars are simply "smudges".
So, my best objects are open clusters and doubles. My priorities are objects due south as those will soon pass into trees. The Northeast objects have some time.
I will often plan based on the part of the sky which will disappear quickly. I identify that region and then begin using Interstellum Deep Sky Atlas (iDSA) and Cambridge Double Star Atlas (CDSA) to identify doubles and clusters. I use a couple of on line sites to identify objects. My limit for doubles is about 4" and I need an open cluster to be at least 5' and have a few stars brighter than 10mag.
Stella Doppe and DSO are great on line tools. I also have a few books and have clipped articles from S&T (Sue French) which provide small scope objects.
I then identify a target star to begin my observing session and use photo copies of iDSA to plan my session with star hopping notes. I write the objects on an index card and use it with the paper copies of charts to see as many objects as possible. A written observation log for each item is written in a notebook with sketching.
After the session, I will index observations to my books with the date observed and will file the paper charts in a folder for the constellation for future reference. Also file the index cards.
One of my goals is to see and resolve as many doubles as possible. I tend to concentrate on a very small area of the sky each session and cover as much of that area as possible...typically one constellation or region of the sky.
At the end, I often will go to favorites such as Double Cluster, M34, M42, M45, gamma Andromedia, etc just for fun before heading back inside.
I have about 30 more days before the weather becomes an issue. I will use both evenings and mornings to catch as many fall and winter objects as possible.