The similarities are more important than the differences for our purposes. Hume is an empiricist and a naturalist (in the philosophical sense) while Kant is a rationalist and an anti-naturalist. But, in the first place, both want to explain our thinking as the outcome of fixed, ahistorical structures. For Hume the structures are psychological and fixed in human nature; for Kant the structures are transcendental and frame all possible thought whatever, including that of martians and angels, if they are rational. Secondly, both agree we are thinking and perceiving at one remove from the things themselves. For Hume all perception is of sentiments or impressions; for Kant sensuous experience or thought yields only representations. In short, all experience is re-presentation of reality in the subjective mode of the experiencer.
It is these two points of aqreement that are our target. I see the subsequent development of philosophy in the 19C as growing insight into the inadequacy of these two ideas: (1) human nature is historically invariant; and (2) reality is never simply present; it is always represented.
The 19C finds everything in motion in the stream of time and at least sometimes that precisely in this temporal unfolding something true in itself is present.
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This is extremely interesting. It seems as though meaning only exists through representation. So that in itself implies that meaning for us, is disconnected from reality. But we connect it to reality all the time. I “hammer” a “nail” into a piece of “wood” many times and construct a “dingy.” The dingy is tangible evidence that meaning exists, I think. So what do we do about this uncertainty? Do we question our motives into an even more misconstrued understanding? Or do we accept things for the way they are? Well maybe we do both. Maybe we question things to the point that we accept that we do things simply because we can and because of the fact they increase the experience of life. That should be the entire foundation of our reasoning. But it’s more complex than that because what makes one individuals experience better makes another’s worse. So how do we solve this problem? Is it even a problem? Or is it a paradox in which only delusion can detach you from?
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