Think Generic
If you only use a single computer, you naturally learn to think in terms of the quirks and features of that computer. If you use many, with many operating systems (e.g. some Windows, some Linux, some Macos), you learn to think more in terms of generic abstract ideas: a file is roughly the same thing on all three OS's, as is a directory (or folder).
Synthesisers
When it comes to synthesisers and music production, it is similar. If we learn only one synth, we will tend to think in terms of the quirks and features of that synth. If, on the other hand, we learn a few, we get a general abstract idea of what an oscillator is, what a filter is, what an envelope is, and what LFO's and modulation matrices are. Armed with such abstract concepts, when we face a new synth, we ask "where are the oscillators?", and "where are the filters?", and "what is the signal path".
The more you can think in such abstract, generic terms, the less you have to learn when faced with a new synthesiser. If you already understand oscillators in a general way, you don't need to relearn that. But if all you know are, say, the oscillators on a Virus, or the oscillators in Serum, then you have more to learn when faced with the details of say, the oscillators in Spire or Zebra.
Learning Synths vs Production Synths
It is always worth keeping the point of a task in mind. Is your aim to get stuff done, or is your aim to learn, or some blend between the two. If your priority is to learn, then perhaps you should look for a synth that is best suited to the learning process: what can you learn the most from? how much of what you learn is transferrable to other synths? And of course where you are in your learning journey. There is no single right choice: what is easy for one may be incomprehensible for another; a piano piece suitable for an advanced player is likely unsuitable for a beginner.
(See also Learning vs Doing.)
DAW's
A similar thing can be said for DAW's. My favourite personally is Reaper. Along with its customisability, it tends to work in terms of a few well-chosen abstractions. There are FX chains, there are tracks, there are items on tracks, sends between tracks, and little else besides machinery to manipulate these. Once you understand those abstractions, then when faced with something like Ableton it is pretty easy to figure out what is going on: you can represent the signal flow and organisation inside Ableton using the same abstractions you learn with Reaper. The reverse, however, isn't true. Someone who only knows Ableton will feel like they've been sat at the console of a spaceship the first time they try Reaper. Now the magic of something like Ableton or Bitwig is in what it does for you, which is what many producers like. However, at some point you need to learn what something like Ableton is doing for you, at the nuts and bolts level.
As an analogue, consider the difference between a manual-shift car and an automatic. If you know how to drive a manual-shift, it isn't too difficult to pick up an automatic; but the reverse isn't true. In the same way, going from something like Reaper to something like Ableton is easier than going in the reverse direction.
In Summary
A limiting factor in understanding something new is the degree to which you can break it down into things you already understand. Well-chosen abstractions, like oscillators, filters, tracks, FX chains, and so on, once understood, provide you the means to easily break down something new into these terms. Even if not everything can be understood in terms of generic abstractions you already understand, you only need to struggle with those things left over, rather than the entire complexity of what you seek to learn.