For some time I helped compile
"The Challenge" which is a monthly set of targets that are designed to showcase different objects, and to appeal to different levels of experience and sized instruments. These objects go from naked eye ones through to objects that require a very large aperture to just make out.
"The Challenge" is not a competition. The challenging part is more a task one set's oneself to push one's experience and understanding of what is actually in the night sky. The monthly collection of targets is not a dumb list, but a select few targets with a description of what it is and what to look for and understand what you are looking at. In many instances, if you come to understand what the essential elements are of a particular object, you can then understand the factors that are influencing other objects of the same type.
While I haven't been able to post a new challenge in a while, the set of monthly Challenges are still current for whatever time of the year it is.
Have a look through the many postings of
"The Challenge". I'm sure you will find it very worthwhile. The actual individual Challenge posts are in the Observational and Visual Forum. The link above is to the Beginners Forum thread where I posted a link to these posts as they were compiled.