There are certain features of our brain structure that are deeply ingrained. One of these is context-dependent memory. Context-dependent memory means that what is learnt in a certain general context is much better remembered, much more quickly recalled and much more applicable to a similar context. In short, if you want to remember something, you have to put yourself in the environment in which you learned it (e.g. go to the same place, listen to the same music, have the same feelings, create the same physical or mental conditions). This may be obvious and understandable, but it has one very important consequence for learning poker.
If you have thought about the history of handicaps, you are absolutely right. Hand history, which is very important, is alien to the context in which poker is actually played. Hand history is a large and confusing block far removed from reality. It has no sense of time, no visual sense and is completely static. A real poker hand has movement, action, experience, emotion. The way you experience the history of a hand is completely different from the way you experience a real hand. What's more, what you learn from hand histories (as well as books, forums) will not apply to the actual game.
This partly explains the existence of players who are good at analysing hands, but are weak in the game. There are many names for this phenomenon: "theory crafters", "keyboard jockeys", etc. These people have developed their skills from the context of hand history, from reading forums or from commenting on players, but they can't apply it all to the actual game of poker.
Once the problem reaches a certain level, it becomes unmanageable. The further we move away from the context, the harder it is to go back. That is just the way it is. How can we avoid such pitfalls?
The first and most effective way would be to try to copy the actual context. For example: do everything you can to make the hand's story as close as possible to a "live" poker hand. Try to trigger all important hands in the hand replayer to get the visual feedback as close as possible to a real poker hand. It may seem like a waste of time, but visual cues will help you transfer what you learn to the real game.
You can also try to visualise the hand as if it were happening in reality. Try 
wake up the area of the brain that is activated by playing poker and accept the stimulus that comes along. Focus your attention and visualise the money, feel what it means to you, see the clock ticking and the right action being taken. The closer you get to the actual experience of the game, the more effective the learning process will be. Go beyond your comfort zone. It may be painful, it may seem silly or even uncomfortable, but it will dramatically improve your skills in the long run.
Something else you can do is to try to "import" the lesson of the history of the hando from the hando through a conversation with yourself. For example, let's say you are reading a hand that is about a great 3-bet river bluff. Instead of just thinking to yourself "Next time I'll do it" (a resolve that almost never materializes), write down an actionable instruction for yourself. For example, "when I can represent a backdoor flush, I will 3-bet the bluff on the river. Keep that piece of paper in plain sight for the next time you do a poker session. Ideally, you should read this instruction from time to time to remind yourself. That way, you'll be more likely to take advantage of a 3-bet bluff on the river when the time is right, and that hand you've been learning will come back to you and you'll want to play it again.
Haseeb Qureshi
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