This is awesome. I love reverse engineering software. There is something so magical about it. I once spent a whole summer reverse engineering crackmes but never moved to actual software hmm.
The idea is you conquer progressively more complicated crackmes and this helps you learn how to tackle random binaries you'll find in the wild.
Generally the step up after crackmes is to find virus payloads/samples and try and unravel those. I understand Stuxnet uses some of the most complex techniques to date: https://www.symantec.com/content/en/us/enterprise/media/secu... (ref: https://news.ycombinator.com/item?id=17099969, also https://news.ycombinator.com/item?id=2212922)
I have an old DOS game I kind of want to kill the collision in so I can play it with my terrible coordination :P
(This is the game: https://www.old-games.org/games/willy - this particular site all is in Hebrew, but it's the only one with this particular version of the game - take a look at the yellow subtext immediately under the title in the screenshot ;P)
Btw, FWIW: I'm roughly around the Sydney area, if I'm interpreting your name right. If Google isn't utterly off base, maybe you're in Brisbane or NSW...? (Many matches for your name, didn't want to take chances poking all of them)