There are many problems in learning history. Here are some of the most important ones:
1. All history is culturally constructed. Hence, all history is from the perspective of a person in a particular setting. Hence, all history is biased. This is also why new histories come out all the time.
2. Similar to point one, all history is necessarily about emphasis and selectivity. Someone makes these decision. Guess what - again we are faced with subjectivity.
3. There is no such things are objective history. This should not surprise you.
4. Also when you deal with the past, there is also the problem of sources. Many things have been lost. And if they exist, it is difficult to interpret.
5. Finally, for a student to master any historical field, it will take time - a lot of time.
In my mind, the problem with learning history is that it deals with an essentially unknowable subject.
History does not consist of names and dates. It consists of stories and lessons. It is about WHY things happen the way they do.
For example, there is no question that there were attacks on the US on 9/11/2001. But there is question as to what caused the attackers to do what they did. The question of WHAT happened is not interesting. The question of WHY it happened most certainly is.
The problem with history is that no one can KNOW why this or any other historical event happened. We can only guess and try to reason it out.
This is a problem because our personal biases determine what stories we will believe about history and no one can ever prove what's true.
This, to me, is the central problem with studying history.
There might be a challenge in the teaching of history and how individuals approach it. I would terms this the difference between believing in a "Consensus" view of history set against a "Conflict" based methodology. Those who believe in teaching the former would tend to side with the notion of American exceptionalism and this would be presented in their pedagogy and philosophy towards the teaching of the discipline. In this belief system, the telling of American History is one steeped in the idea that the American model of historical advancement and political/ economic structure is something that should be modeled by other nations. At some levels, this vision of American History preaches to the idea that history is taught as a retelling of the successes and the glorification of these ideals: The American form of Government is the longest based Constitutional political structure, its method of capitalist based economics "won" and the idea of the acknowledgment of rights, initiated with the American Revolution and continuning through its history, is something to be taught and stressed to students.
This vision of "exceptionalism" is set in stark contrast to the "conflict" point of view. In this setting, the telling of American History is one based on repeated conflicts and this notion of "fight" and "battle" is continued in the modern retelling of American History. Part of this conflict is the acknowledgment of power as being a major element of American History. If one relents in telling this narrative of ongoing conflict, then there is a likelihood to capitulate to silencing the voices of those who battle in this conflict.
At some level, the challenge in learning history might exist in trying to navigate through both polarities of expression historical truth. There might be validity in both expressions, and students, when exposed to both, might have a difficult time in making decisions about what to accept and what to discard. Yet, I would stress that while this is a legitimate challenge in learning history, it allows students to become critical thinkers and gives them a role in the process of deciding how to read and analyze historical narratives of experience.
History is the analysis of fact. It explains why we are where we are. Life is complex; life before our time was no less so. The creation of myth in ancient (and recent!) times serves to simplify the past and make it palatable and acceptable; however, what truths myths contained can be quickly overrun and overlooked by those currently telling and passing on the tale.
Nevertheless, facts are facts. They are immutable, and they are knowable.
The problem of History is that it is not studied nor taught properly. Facts must be framed within the culture that brought them forth; any understanding of events, cause and effect must be within its own time. Where history becomes truly instructive for us in our own time is to witness how prior peoples struggled with the same kinds of conflicts that we have now. Nothing of human experience changes but the names and places. Nothing is new under the Sun.