New user, old nerd and I'm jumping in right here.
My own personal approach to this problem of getting some intuition for ideas of time dilation and length contraction went as follows.
1) Accept that we have no native intuition for such things nor any internal reference points for understanding such a thing. That this is exactly why it took centuries of science to spot this change in descriptions of space, time, matter and relative motion was needed.
It is a counter-intuitive set of results, to the extent that historically it required great contradictions to appear between two sets of very well respected laws to suggest the need for a new theory of space and time. Our experience gives way to a sense of emptiness the moment the rate of relative motion between two observers becomes so appreciable that relativistic effects apply - no human being has ever perceived their everyday world in such a way.
Where these effects are obvious, we have never been. Where they are hidden that's where we live our entire macroscopic lives.
Only in the analysis of small particles where these relative speeds are commonplace revealed the problem was a serious thing and could not be gotten rid of. So the ideas openly defy an intuition, we're just too big and we live in a nicely, gently curved space, so we cannot know anything about this kind of a problem with every intuition we have about space and time, not until it becomes a problem of self-consistency between two sets of very well-loved laws. Then we have two problems, one of them is getting rid of the wrong intuition and the other is not having a new one to put in place. Quite a problem!
But... 1) doesn't mean feeling the same thing as remaining forever uncomfortable with theory and that's because of the self-consistency of the theory and the development of intuition for that instead. So, there's also...
2) That such an intuition for the theory may be carefully developed in spite of not having direct experience of its most shocking effects.
My approach to this was to look at the mathematics a whole lot, look for geometric representations of the theory, read a great many sources, read the original papers by Einstein, Minkowski, etc, all the early relativists who were themselves also still looking to develop such an intuition and familiarity. That kind of sustained effort to get at the relativity theory seemed a worthwhile thing because it isn't like other theories of physics, being a theory of space and time itself, it matters to all coordinate exchange so that places it in a remarkably important place in all theoretical physics. So this thing is, whatever else can be said of it, fundamental to all the physics which comes after it and that's a thing worth persisting with and specifically it's worth persisting in developing intuition for the self-consistency of it, by hook or by crook.
There's also the obvious option on repeating useful thought experiments with subtle variations, just putting yourself in the situation being modeled and imagining yourself inside it. If we cannot have a physical intuition for these effects we need perhaps to try and develop an abstract sense of one, from sheer brute force of imagination.
Humans appear to be absolute naturals at this kind of thinking, so I decided that since we have daydreaming abilities, and reasoning abilities, those were worth coopting for doing a lot of repeated thought experiments to just drill the idea into my brain that this is how the world really is. That everything else I have experienced about time and space has been a kind of pleasant and simplified illusion which comes from living a provincial life, never moving very fast with respect to anything macroscopic, certainly not fast enough to peel away the veil and notice the illusion of absolute space and absolute time is just as much an illusion as an absolute rest frame.
You can see things in your imagination you cannot experience in real life and then check out what you've been thinking about for logical consistency with the theory and that way, over a span of some time, you can definitely train the imagination to have a partial intuition for the observations fitting theory, i.e., intuition for its self-consistency.
It is a kind of like building a jigsaw puzzle when you don't know what the final image looks like but you do know that locally, two pieces always have to fit in a way that makes sense of the images on just those two pieces and so you can still build a jigsaw without knowing anything at all about the global image it contains. So I decided that was a fair way to at least try to attack this kind of problem where there's just no real intuition to start with and everything has to be built up from local efforts of understanding this bit here and that bit there. So just feeding the visual cortex scenarios in which relative motions and such effects would become observable, I claim that's extremely useful, its importance cannot be overstated. And besides, it's amazing to think about and massive fun.
I know it's a kind of silly recommendation but I can still read Mr. Tompkins by Gamow and enjoy that. He wrote one story intended for kids but absolutely good to go as a fun read for adults, covering the special theory of relativity and that's a real gem as starting point for prepping the imagination for repeating interesting thought experiments.
3) just not really ever stopping. It's my view that anyone who says they have mastered this topic, is likely only fooling themselves. The subject is certainly all but bottomless, it is endlessly fascinating to ponder, SR might lose some of its initial mystery but I've been boggled by it for two decades now and its majesty and aura never really seem to fade.