By far the biggest stumbling block in understanding dialectical materialism is understanding dialectics. Like you said yourself, materialism is easier to understand. In order to train your mind in seeing the world dialectically, not necessarily using dialectical materialism but just dialectically, I would actually recommend Daoist works, or more specifically the Daodejing and the Zhuangzi. Both Daoist works investigate the contradictions in all things and how these contradictions interact with one another.

Sample from the Daodejing:

The thirty spokes converge at one hub, but the utility of the cart is a function of the nothingness inside the hub. We throw clay to shape a pot, but the utility of the clay pot is a function of the nothingness inside it. We bore out doors and windows to make a dwelling, but the utility of the dwelling is a function of the nothingness inside it. Thus, it might be something that provides the value, but it is nothing that provides the utility.

The contradiction is between the object, be it a pot, wheel, or house, as it exist and the absence of the object which gives the object its identity. A pot without a hollow inside is just a weirdly shaped brick, a wheel without a hub is just a wooden circular table without legs, a house without an interior is just a small hill. It's only through the absence of the pot that a pot is a pot and not a weirdly shaped brick and so on.

Sample from the Zhuangzi:

Ziqi of Nanbo was wandering around the Hill of Shang when he saw a huge tree there, different from all the rest. A thousand teams of horses could have taken shelter under it, and its shade would have covered them all. Ziqi said, “What tree is this? It must certainly have some extraordinary usefulness!” But looking up, he saw that the smaller limbs were gnarled and twisted, unfit for beams or rafters, and looking down, he saw that the trunk was pitted and rotten and could not be used for coffins. He licked one of the leaves, and it blistered his mouth and made it sore. He sniffed the odor, and it was enough to make a man drunk for three days. “It turns out to be a completely unusable tree,” said Ziqi, “and so it has been able to grow this big. Aha!—it is this unusableness that the Holy Man makes use of!”

There's more before his paragraph, but essentially, it's discussing the usefulness of uselessness. The contradiction is that a useful tree ie a tree with high quality wood, is more likely to be chopped down than a tree that is otherwise useless. It's through its uselessness to humans that it still lives, so it's uselessness to humans is actually one of its greatest asset to itself.

Once you start to internalize being able to see things dialectically, dialectical materialism starts to make a lot more sense while liberal ideas are completely undialectical. For example, strict pacifism is undialectical because it does not acknowledge the dialectical relationship between peace and war as well as not acknowledge the transformation from a violent world to a peace world might be violent. Compare that with the famous Mao quote:

We are advocates of the abolition of war, we do not want war; but war can only be abolished through war, and in order to get rid of the gun it is necessary to take up the gun.

This is a dialectical understanding of war and peace.